CAS No.1235865-77-6,2-((1H-Pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid Suppliers

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2-[(1H-Pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoic acid CAS No.:1235865-77-6 Name: 2-[(1H-P

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2-[(1H-pyrrolo[2,3-B]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethyl ring Hex-1-enyl]methyl]piperazin-1-yl]benzoic acid CAS:1235865-77-6 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating rese

2-[(1H-pyrrolo[2,3-B]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethyl ring Hex-1-enyl]methyl]piperazin-1-yl]benzoic acid CAS:1235865-77-6

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Cas no. 1235865-77-6 2-[(1H-Pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoic acid API or Intermediates Our products are high quality, good price, quick delivery time and we supply

2-[(1H-Pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoic acid

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2-[(1H-Pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoic acid

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Zibo Hangyu Biotechnology Development Co., Ltd

Zibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi

2-((1H-Pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid CAS NO.1235865-77-6

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Henan Tianfu Chemical Co., Ltd.

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CAS1235865-77-6 2-[(1H-Pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoic acid

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2-[(1H-pyrrolo[2,3-B]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethyl ring Hex-1-enyl]methyl]piperazin-1-yl]benzoic acid

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Xiamen Jenny Chemical Technology Co., Ltd.

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2-[(1H-pyrrolo[2,3-B]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylringHex-1-enyl]methyl]piperazin-1-yl]benzoicacid

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Hangzhou Huarong Pharm Co., Ltd.

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2-[(1H-pyrrolo[2,3-B]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethyl ring Hex-1-enyl]methyl]piperazin-1-yl]benzoic acid

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Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd

Name: 2-[(1H-Pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoic acid CAS No.: 1235865-77-6 Formula: C33H35ClN4O3 Structure: Appearance:White Solid Storage:Store sealed at room temp

2-[(1H-Pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoic acid

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Shandong Mopai Biotechnology Co., LTD

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2-((1H-Pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid

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Suzhou Health Chemicals Co., Ltd.

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2-[(1H-Pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoic acid

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Win-Win chemical Co.Ltd

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2-[(1H-pyrrolo[2,3-B]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethyl ring Hex-1-enyl]methyl]piperazin-1-yl]benzoic acid Cas no.1235865-77-6 98%

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Enke Pharma-tech Co.,Ltd. （Cangzhou, China ）

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2-[(1H-Pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoic acid

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2-[(1H-Pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoic acid CAS No.1235865-77-6

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Wuhan Circle Star Chem-medical Technology co.,Ltd.

good quality, competitive price, thoughtful after sale serviceAppearance:white powder Storage:Keep it in dry,shady and cool place Package:25kg,50kg,180kg,200kg,250kg,1000kg，customization Application:Pharma;Industry;Agricultural;chemical reaserch Tran

2-[(1H-Pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoic acid

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Henan Kanbei Chemical Co.,LTD

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Hangzhou ZeErRui Chemical Co., Ltd.

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2-[(1H-pyrrolo[2,3-B]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethyl ring Hex-1-enyl]methyl]piperazin-1-yl]benzoic acid

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HANGZHOU TIANYE CHEMICALS CO., LTD.

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2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid

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Shanghai Terui OP New Material Technology Co., Ltd.

The factory supplies Application:manufacturing supplies

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AstaTech ( Chengdu) BioPharmaceutical Corp.

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2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((4\'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1\'-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid

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Senova Technology Company Limited

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Chemsigma International Co.,Ltd.

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2-(1H-PYRROLO[2,3-B]PYRIDIN-5-YLOXY)-4-(4-((2-(4-CHLOROPHENYL)-4,4-DIMETHYLCYCLOHEX-1-ENYL)METHYL)PIPERAZIN-1-YL)BENZOIC ACID

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Chemlyte Solutions

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Synthetic route

: 1235865-76-5
2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid methyl ester

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; methanol; water at 45℃;	96.9%
With water; sodium hydroxide In tetrahydrofuran; ethanol at 20℃;	93%
With water; sodium hydroxide In dimethyl sulfoxide at 20℃; for 3h; Solvent; Reagent/catalyst; Temperature;	92%

: tert-butyl 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)-oxy)-4-(4-((4′-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1′-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoate

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
With potassium tert-butylate In 2-methyltetrahydrofuran; water for 2h; Inert atmosphere; Large scale;	88%
With potassium tert-butylate In 2-methyltetrahydrofuran; water at 55℃; Inert atmosphere;	85%
With potassium tert-butylate; water In 2-methyltetrahydrofuran at 50℃; for 5h; Inert atmosphere;	57.6%

: C27H33ClN2O3

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Stage #1: C27H33ClN2O3; 5-bromo-1H-pyrrolo[2,3-b]pyridine With copper(l) iodide; caesium carbonate In dimethyl sulfoxide at 80℃; for 3h; Stage #2: With methanol; sodium hydroxide at 65℃; Solvent; Temperature; Reagent/catalyst;	83%

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h 1.2: 24 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran / 0.03 h / -78 °C 2.2: 1 h / -78 - 20 °C 2.3: 1 h / 0 °C 3.1: potassium phosphate / diethylene glycol dimethyl ether / 24 h / 115 °C 4.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 5.1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C 5.2: Cooling View Scheme
Multi-step reaction with 5 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h 1.2: 24 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran / 0.03 h / -78 °C 2.2: 1 h / 20 °C 2.3: 1 h / 0 °C 3.1: potassium phosphate / diethylene glycol dimethyl ether / 24 h / 115 °C 4.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 5.1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C View Scheme
Multi-step reaction with 5 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h 1.2: 24 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.03 h / -78 °C 2.2: 1 h / -78 - 20 °C 3.1: potassium phosphate / diethylene glycol dimethyl ether / 24 h / 115 °C 4.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 5.1: sodium hydroxide; water / 1,4-dioxane / 24 h / 50 °C View Scheme

: 858116-66-2
5-bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran / 0.03 h / -78 °C 1.2: 1 h / -78 - 20 °C 1.3: 1 h / 0 °C 2.1: potassium phosphate / diethylene glycol dimethyl ether / 24 h / 115 °C 3.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 4.1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C 4.2: Cooling View Scheme
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran / 0.03 h / -78 °C 1.2: 1 h / 20 °C 1.3: 1 h / 0 °C 2.1: potassium phosphate / diethylene glycol dimethyl ether / 24 h / 115 °C 3.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 4.1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C View Scheme
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.03 h / -78 °C 1.2: 1 h / -78 - 20 °C 2.1: potassium phosphate / diethylene glycol dimethyl ether / 24 h / 115 °C 3.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 4.1: sodium hydroxide; water / 1,4-dioxane / 24 h / 50 °C View Scheme
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran / 0.03 h / -78 °C 1.2: 1 h / -78 - 20 °C 1.3: 1 h / 0 °C 2.1: potassium phosphate / diethylene glycol dimethyl ether / 24 h / 115 °C 3.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 4.1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C View Scheme
Multi-step reaction with 4 steps 1.1: n-butyllithium; Trimethyl borate / tetrahydrofuran / 1 h / -78 - 20 °C 1.2: 1 h / 0 °C 2.1: potassium phosphate / diethylene glycol dimethyl ether / 24 h / 115 °C 3.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 4.1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C View Scheme

: 32767-46-7
methyl 4,4-dimethyl-2-oxocyclohexancarboxylate

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: sodium hydride / dichloromethane / 0.5 h / 0 °C 1.2: 24 h / -78 - 20 °C 2.1: cesium fluoride / tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; methanol / 24 h / 70 °C 3.1: lithium borohydride; methanol / diethyl ether / 24 h / 20 °C 4.1: triethylamine; methanesulfonyl chloride / dichloromethane / 0.02 h / 0 °C 4.2: 24 h / 20 °C 5.1: trifluoroacetic acid; triethylsilane / dichloromethane / 1 h 6.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 7.1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C 7.2: Cooling View Scheme
Multi-step reaction with 7 steps 1.1: sodium hydride / dichloromethane / 0.5 h / 0 °C 1.2: -78 - 20 °C 2.1: cesium fluoride / tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; methanol / 24 h / 70 °C 3.1: lithium borohydride; methanol / diethyl ether / 24 h / 20 °C 4.1: triethylamine; methanesulfonyl chloride / dichloromethane / 0.02 h / 0 °C 4.2: 24 h / 20 °C 5.1: trifluoroacetic acid; triethylsilane / dichloromethane / 1 h 6.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 7.1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C View Scheme
Multi-step reaction with 7 steps 1.1: sodium hydride / dichloromethane / 0.5 h / 0 °C 1.2: 24 h / -78 - 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0); cesium fluoride / 1,2-dimethoxyethane; methanol / 24 h / 70 °C 3.1: lithium borohydride / methanol / 24 h / 20 °C 4.1: methanesulfonyl chloride; triethylamine / dichloromethane / 0.02 h / 0 °C 4.2: 24 h / 20 °C 5.1: triethylsilane; trifluoroacetic acid / dichloromethane / 1 h 6.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 7.1: sodium hydroxide; water / 1,4-dioxane / 24 h / 50 °C View Scheme

: 1228780-46-8
methyl 4,4-dimethyl-2-(((trifluoromethyl)sulfonyl)oxy)cyclohex-1-ene-1-carboxylate

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: cesium fluoride / tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; methanol / 24 h / 70 °C 2.1: lithium borohydride; methanol / diethyl ether / 24 h / 20 °C 3.1: triethylamine; methanesulfonyl chloride / dichloromethane / 0.02 h / 0 °C 3.2: 24 h / 20 °C 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 1 h 5.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 6.1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C 6.2: Cooling View Scheme
Multi-step reaction with 6 steps 1.1: cesium fluoride / tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; methanol / 24 h / 70 °C 2.1: lithium borohydride; methanol / diethyl ether / 24 h / 20 °C 3.1: triethylamine; methanesulfonyl chloride / dichloromethane / 0.02 h / 0 °C 3.2: 24 h / 20 °C 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 1 h 5.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 6.1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C View Scheme
Multi-step reaction with 6 steps 1.1: tetrakis(triphenylphosphine) palladium(0); cesium fluoride / 1,2-dimethoxyethane; methanol / 24 h / 70 °C 2.1: lithium borohydride / methanol / 24 h / 20 °C 3.1: methanesulfonyl chloride; triethylamine / dichloromethane / 0.02 h / 0 °C 3.2: 24 h / 20 °C 4.1: triethylsilane; trifluoroacetic acid / dichloromethane / 1 h 5.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 6.1: sodium hydroxide; water / 1,4-dioxane / 24 h / 50 °C View Scheme

: 1228780-49-1
4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-carboxylic acid methyl ester

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: lithium borohydride; methanol / diethyl ether / 24 h / 20 °C 2.1: triethylamine; methanesulfonyl chloride / dichloromethane / 0.02 h / 0 °C 2.2: 24 h / 20 °C 3.1: trifluoroacetic acid; triethylsilane / dichloromethane / 1 h 4.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 5.1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C 5.2: Cooling View Scheme
Multi-step reaction with 5 steps 1.1: lithium borohydride; methanol / diethyl ether / 24 h / 20 °C 2.1: triethylamine; methanesulfonyl chloride / dichloromethane / 0.02 h / 0 °C 2.2: 24 h / 20 °C 3.1: trifluoroacetic acid; triethylsilane / dichloromethane / 1 h 4.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 5.1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C View Scheme
Multi-step reaction with 5 steps 1.1: lithium borohydride / methanol / 24 h / 20 °C 2.1: methanesulfonyl chloride; triethylamine / dichloromethane / 0.02 h / 0 °C 2.2: 24 h / 20 °C 3.1: triethylsilane; trifluoroacetic acid / dichloromethane / 1 h 4.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 5.1: sodium hydroxide; water / 1,4-dioxane / 24 h / 50 °C View Scheme

: 1228780-51-5
(4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methanol

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triethylamine; methanesulfonyl chloride / dichloromethane / 0.02 h / 0 °C 1.2: 24 h / 20 °C 2.1: trifluoroacetic acid; triethylsilane / dichloromethane / 1 h 3.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 4.1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C 4.2: Cooling View Scheme
Multi-step reaction with 4 steps 1.1: triethylamine; methanesulfonyl chloride / dichloromethane / 0.02 h / 0 °C 1.2: 24 h / 20 °C 2.1: trifluoroacetic acid; triethylsilane / dichloromethane / 1 h 3.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 4.1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C View Scheme
Multi-step reaction with 4 steps 1.1: methanesulfonyl chloride; triethylamine / dichloromethane / 0.02 h / 0 °C 1.2: 24 h / 20 °C 2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 1 h 3.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 4.1: sodium hydroxide; water / 1,4-dioxane / 24 h / 50 °C View Scheme

: 1228780-71-9
tert-butyl 4-((4′-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1′-biphenyl]-2-yl)methyl)piperazine-1-carboxylate

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: trifluoroacetic acid; triethylsilane / dichloromethane / 1 h 2.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 3.1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C 3.2: Cooling View Scheme
Multi-step reaction with 3 steps 1: trifluoroacetic acid; triethylsilane / dichloromethane / 1 h 2: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 3: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C View Scheme
Multi-step reaction with 3 steps 1: triethylsilane; trifluoroacetic acid / dichloromethane / 1 h 2: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 3: sodium hydroxide; water / 1,4-dioxane / 24 h / 50 °C View Scheme

: 1228780-72-0
1-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1‘-biphenyl]-2-yl)methyl)piperazine

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 2.1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C 2.2: Cooling View Scheme
Multi-step reaction with 2 steps 1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 2: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C View Scheme
Multi-step reaction with 2 steps 1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 2: sodium hydroxide; water / 1,4-dioxane / 24 h / 50 °C View Scheme

: 685514-01-6
1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridin-5-ol

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium phosphate / diethylene glycol dimethyl ether / 24 h / 115 °C 2.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 3.1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C 3.2: Cooling View Scheme
Multi-step reaction with 3 steps 1: potassium phosphate / diethylene glycol dimethyl ether / 24 h / 115 °C 2: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 3: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C View Scheme
Multi-step reaction with 3 steps 1: potassium phosphate / diethylene glycol dimethyl ether / 24 h / 115 °C 2: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 3: sodium hydroxide; water / 1,4-dioxane / 24 h / 50 °C View Scheme
Multi-step reaction with 3 steps 1: potassium phosphate / diethylene glycol dimethyl ether / 24 h / 115 °C 2: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 3: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C View Scheme
Multi-step reaction with 3 steps 1: potassium phosphate / diethylene glycol dimethyl ether / 24 h / 115 °C 2: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 3: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C View Scheme

: 1235865-75-4
2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-fluorobenzoic acid methyl ester

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 2.1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C 2.2: Cooling View Scheme
Multi-step reaction with 2 steps 1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 2: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C View Scheme
Multi-step reaction with 2 steps 1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 2: sodium hydroxide; water / 1,4-dioxane / 24 h / 50 °C View Scheme

: 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-bromobenzoic acid tert-butyl ester

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium phosphate / toluene / 0.5 h 1.2: 16 h / 55 °C / Inert atmosphere 2.1: potassium tert-butylate / water; 2-methyltetrahydrofuran / 55 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 0 h / 20 - 25 °C 1.2: 60 - 65 °C 2.1: (4-(N,N-dimethylamino)phenyl)-di-tert-butylphosphine; tris-(dibenzylideneacetone)dipalladium(0); lithium hexamethyldisilazane / tetrahydrofuran; toluene / 0.5 h / 55 - 56 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); (4-(N,N-dimethylamino)phenyl)-di-tert-butylphosphine / tetrahydrofuran; toluene / Inert atmosphere; Large scale 2: potassium tert-butylate / water; 2-methyltetrahydrofuran / 2 h / Inert atmosphere; Large scale View Scheme
Multi-step reaction with 2 steps 1.1: sodium t-butanolate / toluene; tetrahydrofuran / 0.75 h / 20 °C / Inert atmosphere 1.2: 18 h / 70 °C / Inert atmosphere 2.1: potassium tert-butylate; water / 2-methyltetrahydrofuran / 5 h / 50 °C / Inert atmosphere View Scheme

: 2979-19-3
3,3-dimethylcyclohexanone

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: trichlorophosphate / dichloromethane / 1.83 h / -5 - 20 °C 1.2: 21 h / 5 °C / Reflux 2.1: tetrabutylammomium bromide / acetonitrile / 0.08 h / 20 °C 2.2: 0.08 h / 20 °C 2.3: 15 h / 30 - 35 °C / Inert atmosphere 3.1: tetrahydrofuran; toluene / 0.08 h / 20 °C 3.2: 4 h / 25 °C 4.1: hydrogenchloride / water; isopropyl alcohol / 12 h / 65 °C 5.1: potassium phosphate / toluene / 0.5 h 5.2: 16 h / 55 °C / Inert atmosphere 6.1: potassium tert-butylate / water; 2-methyltetrahydrofuran / 55 °C / Inert atmosphere View Scheme
Multi-step reaction with 7 steps 1.1: sodium hydride / tetrahydrofuran / Reflux; Inert atmosphere 1.2: 4 h / Reflux 2.1: sodium hydride / dichloromethane / 0.83 h / 0 °C 2.2: -78 - 20 °C 3.1: tetrakis(triphenylphosphine) palladium(0); potassium fluoride / methanol; 1,2-dimethoxyethane / 16 h / 65 °C / Inert atmosphere 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 5.1: triethylamine; methanesulfonyl chloride / dichloromethane / 0.05 h / 0 °C 5.2: 24 h / 0 °C 6.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 140 °C / Inert atmosphere 7.1: sodium hydroxide / tetrahydrofuran; methanol; water / 45 °C View Scheme
Multi-step reaction with 6 steps 1.1: trichlorophosphate / dichloromethane / 1 h / 0 - 20 °C 1.2: 0 - 50 °C 2.1: tetrabutylammomium bromide; potassium carbonate; palladium diacetate / tetrahydrofuran; water / 30 - 35 °C / Inert atmosphere 3.1: sodium tetrahydroborate; methanol / 2 h / 0 - 5 °C 4.1: phosphorus tribromide; pyridine / cyclohexane / 2 h / 2 - 5 °C 5.1: triethylamine / tetrahydrofuran / 3 h / 67 °C 6.1: sodium hydroxide; water / dimethyl sulfoxide / 3 h / 20 °C View Scheme

: 1228943-80-3
2-chloro-4,4-dimethyl-2-oxocyclohexenecarbaldehyde

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: tetrabutylammomium bromide / acetonitrile / 0.08 h / 20 °C 1.2: 0.08 h / 20 °C 1.3: 15 h / 30 - 35 °C / Inert atmosphere 2.1: tetrahydrofuran; toluene / 0.08 h / 20 °C 2.2: 4 h / 25 °C 3.1: hydrogenchloride / water; isopropyl alcohol / 12 h / 65 °C 4.1: potassium phosphate / toluene / 0.5 h 4.2: 16 h / 55 °C / Inert atmosphere 5.1: potassium tert-butylate / water; 2-methyltetrahydrofuran / 55 °C / Inert atmosphere View Scheme
Multi-step reaction with 5 steps 1: tetrabutylammomium bromide; potassium carbonate; palladium diacetate / tetrahydrofuran; water / 30 - 35 °C / Inert atmosphere 2: sodium tetrahydroborate; methanol / 2 h / 0 - 5 °C 3: phosphorus tribromide; pyridine / cyclohexane / 2 h / 2 - 5 °C 4: triethylamine / tetrahydrofuran / 3 h / 67 °C 5: sodium hydroxide; water / dimethyl sulfoxide / 3 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: potassium carbonate; tetrabutylammomium bromide; tetrakis(triphenylphosphine) palladium(0) / water; acetonitrile / 15 h / 60 °C / Inert atmosphere 2.1: sodium tris(acetoxy)borohydride / toluene; tetrahydrofuran / 8 h / 20 °C 2.2: 5 h / 70 °C 3.1: sodium t-butanolate / toluene; tetrahydrofuran / 0.75 h / 20 °C / Inert atmosphere 3.2: 18 h / 70 °C / Inert atmosphere 4.1: potassium tert-butylate; water / 2-methyltetrahydrofuran / 5 h / 50 °C / Inert atmosphere View Scheme

: 1228837-05-5
4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-carbaldehyde

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: tetrahydrofuran; toluene / 0.08 h / 20 °C 1.2: 4 h / 25 °C 2.1: hydrogenchloride / water; isopropyl alcohol / 12 h / 65 °C 3.1: potassium phosphate / toluene / 0.5 h 3.2: 16 h / 55 °C / Inert atmosphere 4.1: potassium tert-butylate / water; 2-methyltetrahydrofuran / 55 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 0.17 h / 32 °C 1.2: 20 h / 5 °C 2.1: water; lithium hydroxide / tetrahydrofuran / 64 h / 32 - 65 °C View Scheme
Multi-step reaction with 4 steps 1: sodium tetrahydroborate; methanol / 2 h / 0 - 5 °C 2: phosphorus tribromide; pyridine / cyclohexane / 2 h / 2 - 5 °C 3: triethylamine / tetrahydrofuran / 3 h / 67 °C 4: sodium hydroxide; water / dimethyl sulfoxide / 3 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1: sodium tris(acetoxy)borohydride / tetrahydrofuran; toluene / 20 °C / Inert atmosphere; Large scale 2: hydrogenchloride / isopropyl alcohol; water / Inert atmosphere; Large scale 3: potassium phosphate / toluene; water / 0.5 h / 25 °C / Inert atmosphere 4: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); (4-(N,N-dimethylamino)phenyl)-di-tert-butylphosphine / tetrahydrofuran; toluene / Inert atmosphere; Large scale 5: potassium tert-butylate / water; 2-methyltetrahydrofuran / 2 h / Inert atmosphere; Large scale View Scheme
Multi-step reaction with 3 steps 1.1: sodium tris(acetoxy)borohydride / toluene; tetrahydrofuran / 8 h / 20 °C 1.2: 5 h / 70 °C 2.1: sodium t-butanolate / toluene; tetrahydrofuran / 0.75 h / 20 °C / Inert atmosphere 2.2: 18 h / 70 °C / Inert atmosphere 3.1: potassium tert-butylate; water / 2-methyltetrahydrofuran / 5 h / 50 °C / Inert atmosphere View Scheme

: 889858-12-2
4-bromo-2-fluoro-benzoic acid tert-butyl ester

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium t-butanolate / N,N-dimethyl-formamide / 0 - 50 °C 2.1: potassium phosphate / toluene / 0.5 h 2.2: 16 h / 55 °C / Inert atmosphere 3.1: potassium tert-butylate / water; 2-methyltetrahydrofuran / 55 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; acetonitrile / 0 h / 20 - 25 °C 1.2: 24 h / 20 - 95 °C 2.1: tetrahydrofuran / 0 h / 20 - 25 °C 2.2: 60 - 65 °C 3.1: (4-(N,N-dimethylamino)phenyl)-di-tert-butylphosphine; tris-(dibenzylideneacetone)dipalladium(0); lithium hexamethyldisilazane / tetrahydrofuran; toluene / 0.5 h / 55 - 56 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: potassium tert-butylate / N,N-dimethyl-formamide / 8 h / 0 - 55 °C / Inert atmosphere; Large scale 2: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); (4-(N,N-dimethylamino)phenyl)-di-tert-butylphosphine / tetrahydrofuran; toluene / Inert atmosphere; Large scale 3: potassium tert-butylate / water; 2-methyltetrahydrofuran / 2 h / Inert atmosphere; Large scale View Scheme
Multi-step reaction with 3 steps 1.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 10 h / 100 °C 2.1: sodium t-butanolate / toluene; tetrahydrofuran / 0.75 h / 20 °C / Inert atmosphere 2.2: 18 h / 70 °C / Inert atmosphere 3.1: potassium tert-butylate; water / 2-methyltetrahydrofuran / 5 h / 50 °C / Inert atmosphere View Scheme

: 105931-73-5
1-bromo-3-fluoro-4-iodobenzene

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: isopropylmagnesium chloride / tetrahydrofuran / 1 h / -5 - 0 °C 1.2: 1 h 2.1: sodium t-butanolate / N,N-dimethyl-formamide / 0 - 50 °C 3.1: potassium phosphate / toluene / 0.5 h 3.2: 16 h / 55 °C / Inert atmosphere 4.1: potassium tert-butylate / water; 2-methyltetrahydrofuran / 55 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1.1: isopropylmagnesium chloride / tetrahydrofuran / 1 h / -5 - 0 °C / Inert atmosphere; Large scale 1.2: 1 h / 0 - 5 °C / Inert atmosphere; Large scale 2.1: potassium tert-butylate / N,N-dimethyl-formamide / 8 h / 0 - 55 °C / Inert atmosphere; Large scale 3.1: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); (4-(N,N-dimethylamino)phenyl)-di-tert-butylphosphine / tetrahydrofuran; toluene / Inert atmosphere; Large scale 4.1: potassium tert-butylate / water; 2-methyltetrahydrofuran / 2 h / Inert atmosphere; Large scale View Scheme
Multi-step reaction with 4 steps 1.1: isopropylmagnesium chloride / tetrahydrofuran / 1 h / -10 - -5 °C 1.2: 1 h / -5 - 0 °C 2.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 10 h / 100 °C 3.1: sodium t-butanolate / toluene; tetrahydrofuran / 0.75 h / 20 °C / Inert atmosphere 3.2: 18 h / 70 °C / Inert atmosphere 4.1: potassium tert-butylate; water / 2-methyltetrahydrofuran / 5 h / 50 °C / Inert atmosphere View Scheme

: 1679-18-1
4-Chlorophenylboronic acid

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: cesium fluoride; tetrakis(triphenylphosphine) palladium(0) / methanol; 1,2-dimethoxyethane / 24 h / 70 °C 2.1: lithium borohydride; methanol / diethyl ether / 24 h / 20 °C 3.1: methanesulfonyl chloride; triethylamine / dichloromethane / 0.02 h / 0 °C 3.2: 24 h / 20 °C 4.1: triethylsilane; trifluoroacetic acid / dichloromethane / 1 h 5.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C 6.1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: cesium fluoride; tetrakis(triphenylphosphine) palladium(0) / methanol; 1,2-dimethoxyethane / 24 h / 70 °C
2.1: lithium borohydride; methanol / diethyl ether / 24 h / 20 °C
3.1: methanesulfonyl chloride; triethylamine / dichloromethane / 0.02 h / 0 °C
3.2: 24 h / 20 °C
4.1: triethylsilane; trifluoroacetic acid / dichloromethane / 1 h
5.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C
6.1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C
View Scheme

: C16H21ClO3S

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 50 °C / Inert atmosphere 2: sodium hydroxide; water / tetrahydrofuran; ethanol / 20 °C View Scheme

: 392-09-6
2-fluoro-4-nitro-benzoic acid methyl ester

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C / Inert atmosphere 2: hydrogen; palladium 10% on activated carbon / methanol / 760.05 Torr 3: potassium carbonate / tert-butyl alcohol / 48 h 4: potassium carbonate / N,N-dimethyl-formamide / 50 °C / Inert atmosphere 5: sodium hydroxide; water / tetrahydrofuran; ethanol / 20 °C View Scheme

: C15H11N3O5

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogen; palladium 10% on activated carbon / methanol / 760.05 Torr 2: potassium carbonate / tert-butyl alcohol / 48 h 3: potassium carbonate / N,N-dimethyl-formamide / 50 °C / Inert atmosphere 4: sodium hydroxide; water / tetrahydrofuran; ethanol / 20 °C View Scheme

: C15H13N3O3

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / tert-butyl alcohol / 48 h 2: potassium carbonate / N,N-dimethyl-formamide / 50 °C / Inert atmosphere 3: sodium hydroxide; water / tetrahydrofuran; ethanol / 20 °C View Scheme

: methyl (2-((1H-pyrrole[2,3-b]pyridin-5-yl)oxy)-4-(piperazin-1-yl))benzoate

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 50 °C / Inert atmosphere 2: sodium hydroxide; water / tetrahydrofuran; ethanol / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 0.17 h / 32 °C 1.2: 20 h / 5 °C 2.1: water; lithium hydroxide / tetrahydrofuran / 64 h / 32 - 65 °C View Scheme
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 3 h / 67 °C 2: sodium hydroxide; water / dimethyl sulfoxide / 3 h / 20 °C View Scheme

: 98549-88-3
5-hydroxypyrrolo[2,3-b]pyridine

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C / Inert atmosphere 2: hydrogen; palladium 10% on activated carbon / methanol / 760.05 Torr 3: potassium carbonate / tert-butyl alcohol / 48 h 4: potassium carbonate / N,N-dimethyl-formamide / 50 °C / Inert atmosphere 5: sodium hydroxide; water / tetrahydrofuran; ethanol / 20 °C View Scheme
Multi-step reaction with 3 steps 1: potassium phosphate heptahydrate / diethylene glycol dimethyl ether / 115 °C / Inert atmosphere 2: dipotassium hydrogenphosphate / dimethyl sulfoxide / 140 °C / Inert atmosphere 3: sodium hydroxide / tetrahydrofuran; methanol; water / 45 °C View Scheme
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide; acetonitrile / 0 h / 20 - 25 °C 1.2: 26 h / 20 - 95 °C 1.3: 0.5 h / 60 - 95 °C 2.1: (4-(N,N-dimethylamino)phenyl)-di-tert-butylphosphine; tris-(dibenzylideneacetone)dipalladium(0); lithium hexamethyldisilazane / tetrahydrofuran; toluene / 0.5 h / 55 - 56 °C / Inert atmosphere View Scheme

: 106614-28-2
methyl 2,4-difluorobenzoate

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium phosphate heptahydrate / diethylene glycol dimethyl ether / 115 °C / Inert atmosphere 2: dipotassium hydrogenphosphate / dimethyl sulfoxide / 140 °C / Inert atmosphere 3: sodium hydroxide / tetrahydrofuran; methanol; water / 45 °C View Scheme
Multi-step reaction with 3 steps 1.1: potassium phosphate / 1,4-dioxane / 47 h / 34 - 90 °C 2.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 0.08 h / 29 °C / Inert atmosphere 2.2: 24.08 h / 29 - 120 °C 3.1: water; lithium hydroxide / tetrahydrofuran / 64 h / 32 - 65 °C View Scheme
Multi-step reaction with 4 steps 1: potassium phosphate / diethylene glycol dimethyl ether / 110 °C 2: dimethyl sulfoxide / 2 h / 90 °C 3: triethylamine / tetrahydrofuran / 3 h / 67 °C 4: sodium hydroxide; water / dimethyl sulfoxide / 3 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: potassium phosphate / diethylene glycol dimethyl ether / 10 h / 115 °C / Inert atmosphere 2: dipotassium hydrogenphosphate / dimethyl sulfoxide / 12 h / 140 °C / Inert atmosphere 3: sodium hydroxide; water / tetrahydrofuran; methanol / 10 h / 45 °C View Scheme

: 1228780-72-0
1-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1‘-biphenyl]-2-yl)methyl)piperazine

: 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-bromobenzoic acid

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); (4-(N,N-dimethylamino)phenyl)-di-tert-butylphosphine; lithium hexamethyldisilazane In tetrahydrofuran; toluene at 55 - 56℃; for 0.5h; Inert atmosphere;

: 1-((4′-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1′-biphenyl]-2-yl)methyl) piperazine dihydrochloride

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium phosphate / toluene; water / 0 h / 20 - 25 °C 2: (4-(N,N-dimethylamino)phenyl)-di-tert-butylphosphine; tris-(dibenzylideneacetone)dipalladium(0); lithium hexamethyldisilazane / tetrahydrofuran; toluene / 0.5 h / 55 - 56 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: potassium phosphate / toluene; water / 0.5 h / 25 °C / Inert atmosphere 2: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); (4-(N,N-dimethylamino)phenyl)-di-tert-butylphosphine / tetrahydrofuran; toluene / Inert atmosphere; Large scale 3: potassium tert-butylate / water; 2-methyltetrahydrofuran / 2 h / Inert atmosphere; Large scale View Scheme

: 179232-29-2
methyl 4-bromo-2-fluorobenzoate

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide; acetonitrile / 0 h / 20 - 25 °C 1.2: 26 h / 20 - 95 °C 1.3: 0.5 h / 60 - 95 °C 2.1: (4-(N,N-dimethylamino)phenyl)-di-tert-butylphosphine; tris-(dibenzylideneacetone)dipalladium(0); lithium hexamethyldisilazane / tetrahydrofuran; toluene / 0.5 h / 55 - 56 °C / Inert atmosphere View Scheme

: 406233-31-6
4-fluoro-3-nitrobenzenesulfonamide

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methyl)piperazin-1-yl)-N-((4-fluoro-3-nitrophenyl)sulfonyl)benzamide

Conditions

Conditions	Yield
With trichlorophosphate at 85℃; for 5h;	100%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20 - 30℃; for 16h; Solvent; Temperature; Reagent/catalyst;	96.3%

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: 97-09-6
4-Chloro-3-nitrobenzenesulfonamide

: 1257044-99-7
4-(4-{[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-en-1-yl]methyl}piperazin-1-yl)-N-[(3-nitro-4-chlorophenyl)sulfonyl]-2-{1H-pyrrolo[2,3-b]pyridin-5-yloxy}benzamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20 - 30℃; for 16h;	96.8%

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: 2-[(1H-pyrrolo[2,3-b]pyridine-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoic acid sulfate

Conditions

Conditions	Yield
With sulfuric acid In tetrahydrofuran at 50 - 55℃; for 0.5h;	92%

: 1228779-96-1
3-nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: 1257044-40-8
2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1-biphenyl]-2-yl)methyl)piperazin-1-yl)-N-((3-nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)phenyl)sulfonyl)benzamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 3h; Reagent/catalyst; Temperature;	91.4%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 25℃; for 12h; Inert atmosphere; Large scale;	86%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 25℃;	84%

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: 104-15-4
toluene-4-sulfonic acid

: 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro[1,1‘-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid p-toluenesulfonic acid salt

Conditions

Conditions	Yield
In acetone at 20 - 30℃;	86.92%

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: 76-05-1
trifluoroacetic acid

: 2-[(1H-pyrrolo[2,3-b]pyridine-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoic acid trifluoroacetic acid salt

Conditions

Conditions	Yield
In tetrahydrofuran at 50 - 55℃; for 0.5h;	85%

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: 8-(2-nitro-4-aminosulfonylphenylamino)octanoic acid ethyl ester

: ethyl 8-((4-(N-(2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoyl)sulfamoyl)-2-nitrophenyl)amino)octanoate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	85%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	85%

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: C17H26N4O6S

: tert-butyl 4-((4-(N-(2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)-4-(4-((2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl)methyl)piperazin-1-yl)benzoyl)sulfamoyl)-2-nitrophenylamino)methyl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃;	79%

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: 6-(2-nitro-4-sulfamoylphenoxy)-2-azaspiro[3.3]heptane-2-carboxylic acid tert-butyl ester

: 6-(4-(N-(2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoyl)sulfamoyl)-2-nitrophenoxy)-2-azaspiro[3.3]heptane-2-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16h;	77.07%

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: 3-nitro-4-((((2R,3R,4R,5R)-3,4,5-tris((trimethylsilyl)oxy)tetrahydrofuran-2-yl)methyl)amino)benzenesulfonamide

: C44H48ClN7O10S

Conditions

Conditions	Yield
Stage #1: [2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]; 3-nitro-4-((((2R,3R,4R,5R)-3,4,5-tris((trimethylsilyl)oxy)tetrahydrofuran-2-yl)methyl)amino)benzenesulfonamide With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; Stage #2: With acetic acid; N,N`-dimethylethylenediamine In dichloromethane at 55℃;	63%

Yield

Stage #1: [2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]; 3-nitro-4-((((2R,3R,4R,5R)-3,4,5-tris((trimethylsilyl)oxy)tetrahydrofuran-2-yl)methyl)amino)benzenesulfonamide With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃;
Stage #2: With acetic acid; N,N`-dimethylethylenediamine In dichloromethane at 55℃;

63%

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: 101-83-7
N-cyclohexyl-cyclohexanamine

: 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro[1,1‘-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid dicyclohexylamine salt

Conditions

Conditions	Yield
In methanol; acetone at 20 - 30℃;	60.6%

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: C32H46N4O12S

: C65H79ClN8O14S

Conditions

Conditions	Yield
Stage #1: [2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid] With 4-pyrrolidin-1-ylpyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.5h; Cooling with ice; Stage #2: C32H46N4O12S In dichloromethane at 20℃; for 24h;	58.1%

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: sodium 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((4-chloro-5,5-dimethyl-3,4,5,6-tetrahydro[1,1‘-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoate

Conditions

Conditions	Yield
With sodium 2-ethylhexenoate In ethyl acetate at 20 - 30℃; for 16h;	57.08%

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: 2-nitro-4-sulfamoylphenyl trifluoromethanesulfonate

: 4-(N-(2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methyl)piperazine-1-yl)benzoyl)sulfamoyl)-2-nitrophenyl trifluoromethanesulfonate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 3h;	53.9%

: 1228779-96-1
3-nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: venetoclax sodium

Conditions

Conditions	Yield
Stage #1: 3-nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide; [2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid] With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Stage #2: With sodium hydroxide In methanol at 55 - 60℃; for 2h;	53%

Yield

Stage #1: 3-nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide; [2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid] With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;
Stage #2: With sodium hydroxide In methanol at 55 - 60℃; for 2h;

53%

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: 4-(2-(4-oxaspiro[2.4]heptan-6-yloxy)ethoxy)-3-nitrobenzenesulfonamide

: 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-N-((4-(2-(4-oxaspiro[2.4]heptan-6-yloxy)ethoxy)-3-nitrophenyl)sulfonyl)-4-(4-((4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methyl)piperazine-1-yl)benzamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃;	49%

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: C27H38N4O11S

: C60H71ClN8O13S

Conditions

Conditions	Yield
Stage #1: [2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid] With 4-pyrrolidin-1-ylpyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.5h; Cooling with ice; Stage #2: C27H38N4O11S In dichloromethane at 20℃; for 24h;	47.8%

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: (2-nitro-4-sulfamoylphenyl)glycine methyl ester

: (4-(N-(2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((4'-chloro-5,5-dimethyltetrahydro-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoyl)sulfamoyl)-2-nitrophenyl)glycine ethyl ester

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;	47.4%

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: C33H46N4O14S

: C66H79ClN8O16S

Conditions

Conditions	Yield
Stage #1: [2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid] With 4-pyrrolidin-1-ylpyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.5h; Cooling with ice; Stage #2: C33H46N4O14S In dichloromethane at 20℃; for 24h;	40.4%

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: 4-((4-oxaspiro[2.4]heptan-6-yl)oxy)-3-nitrobenzenesulfonamide

: 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-N-((4-(4-oxaspiro[2.4]heptan-6-yloxy)3-nitrophenyl)sulfonyl)-4-(4-((4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methyl)piperazine-1-yl)benzamide

Conditions

Conditions	Yield
With dmap In dichloromethane at 0 - 20℃;	35%

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: C12H15(2)H2N3O5S

: C45H48(2)H2ClN7O7S

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 10h;	33%

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: C19H31N5O6S

: C52H64ClN9O8S

Conditions

Conditions	Yield
Stage #1: [2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid] With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: C19H31N5O6S In dichloromethane at 0 - 20℃; Inert atmosphere;	11%

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: C19H26N6O4S

: C52H59ClN10O6S

Conditions

Conditions	Yield
Stage #1: [2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid] With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: C19H26N6O4S In dichloromethane at 0 - 20℃; Inert atmosphere;	10%

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: 1257046-28-8
(R)-3-nitro-4-(1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-3-ylamino)benzenesulfonamide

: 1257046-27-7
4-(4-{[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-en-1-yl]methyl}piperazin-1-yl)-N-[(3-nitro-4-{[(3R)-1-tetrahydro-2H-pyran-4-ylpyrrolidin-3-yl]amino}phenyl)sulfonyl]-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane; N,N-dimethyl-formamide for 18h;
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane; N,N-dimethyl-formamide for 18h;

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: 1256546-39-0
5-chloro-6-((4-fluoro-1-(oxetan-3-yl)piperidin-4-yl)methoxy)pyridine-3-sulfonamide

: 1257049-26-5
N-[(5-chloro-6-{[4-fluoro-1-(oxetan-3-yl)piperidin-4-yl]methoxy}pyridin-3-yl)sulfonyl]-4-(4-{[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-en-1-yl]methyl}piperazin-1-yl)-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: 1228836-22-3
(S)-3-nitro-4-((tetrahydro-2H-pyran-3-yl)methylamino)benzenesulfonamide

: 1257044-51-1
4-(4-{[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-en-1-yl]methyl}piperazin-1-yl)-N-[(3-nitro-4-{[(3S)-tetrahydro-2H-pyran-3-ylmethyl]amino}phenyl)sulfonyl]-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzamide

Conditions

Yield

Stage #1: [2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]; (S)-3-nitro-4-((tetrahydro-2H-pyran-3-yl)methylamino)benzenesulfonamide With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;
Stage #2: With trifluoroacetic acid In water; acetonitrile
Stage #3: With sodium hydrogencarbonate In dichloromethane; water

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;

: 1235865-77-6
[2-((1H-pyrrolo [2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid]

: 4-((((1r,4r)-4-hydroxy-4-methylcyclohexyl)methyl)amino)-3-nitrobenzenesulfonamide

: 4-(4-{[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-en-1-yl]methyl}piperazin-1-yl)-N-[(4-{[(trans-4-hydroxy-4-methylcyclohexyl)methyl]amino}-3-nitrophenyl)sulfonyl]-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane

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CAS No.:1235865-77-6
Name:2-((1H-Pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid
Article Data:20
Molecular Structure:
Formula:C33H35ClN4O3
Molecular Weight:571.119
Synonyms:1235865-77-6;2-((1H-Pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid;2-[(1H-Pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoic acid;4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzoic acid;EC 805-126-7;2-((1H-Pyrrolo(2,3-b)pyridin-5-yl)oxy)-4-(4-((4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-(1,1'-biphenyl)-2-yl)methyl)piperazin-1-yl)benzoic acid;C33H35ClN4O3;SCHEMBL523382;DTXSID301102949;BCP09745;CS-M3716;MFCD28129979;AKOS027254177;SB18336;4-[4-[[2-(4-chlorophenyl)-4,4-dimethyl-1-cyclohexen-1-yl]methyl]-1-piperazinyl]-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)Benzoic acid;AC-29701;DS-10365;FT-0742099;2-((1H-Pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic;2-((1H-Pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoicacid;2-(1H-Pyrrolo[2,3-b]py-5-yloxy)-4-(4-(4'-Cl-5,5-diMe-3,4,5,6-tetrahydro-1,1'-biPh-2-yl)methylpiperazin-1-yl)benzoic acid, 95%;2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)-4-(4-((2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl)methyl)piperazin-1-yl)benzamide;2-(1h-pyrrolo[2,3-b]pyridin-5-yloxy)-4-(4-((2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl)methyl)piperazin-1-yl)benzoic acid;4-(4-{[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-en-1-yl]methyl}piperazin-1-yl)-2-{1H-pyrrolo[2,3-b]pyridin-5-yloxy}benzoic acid;4-[4-[[2-(4-chlorophenyl)-4,4-dimethyl-cyclohexen-1-yl]methyl]piperazin-1-yl]-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzoic acid;Benzoic acid, 4-[4-[[2-(4-chlorophenyl)-4,4-dimethyl-1-cyclohexen-1-yl]methyl]-1-piperazinyl]-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)-
EINECS:805-126-7
Density:1.282±0.06 g/cm3(Predicted)
Melting Point:
Boiling Point:
Flash Point:
Solubility:
Appearance:
Hazard Symbols:
Risk Codes
Safety:
Transport Information:
PSA:81.69000
LogP:7.49560

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