CAS No.1235865-76-5,Methyl 2-[(1H-pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoate Suppliers

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Methyl 2-[(1H-pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoate

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Henan Wentao Chemical Product Co., Ltd.

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Methyl 2-[(1H-pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoate

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Methyl 2-[(1H-pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoate

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Zibo Hangyu Biotechnology Development Co., Ltd

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Methyl 2-[(1H-pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoate

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Zibo Dorne chemical technology co. LTD

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Methyl 2-[(1H-pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoate

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Methyl2-[(1H-pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoate

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Methyl 2-[(1H-pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoate

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TAIZHOU ZHENYU BIOTECHNOLOGY CO., LTD

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Methyl 2-[(1H-pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoate

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Xian Changyue Biological Technology Co., Ltd.

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Methyl 2-[(1H-pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoate

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Antimex Chemical Limied

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Methyl 2-[(1H-pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoate

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Guangdong Juda Chemical Industrial Co.,Limited

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Methyl 2-[(1H-pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoate CAS No.1235865-76-5

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DB BIOTECH CO., LTD

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Methyl 2-[(1H-pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoate

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Henan Kanbei Chemical Co.,LTD

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Methyl 2-[(1H-pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoate

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HANGZHOU TIANYE CHEMICALS CO., LTD.

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Methyl 2-[(1H-pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoate

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Wuhan Bright Chemical Co., Ltd.

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Methyl 2-[(1H-pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoate

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Chemlyte Solutions

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Methyl 2-[(1H-pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoate

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Methyl2-[(1H-pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoate

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Hebei Muhuang Technology Co., Ltd

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Methyl 2-[(1H-pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoate

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AstaTech ( Chengdu) BioPharmaceutical Corp.

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methyl 2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)-4-(4-((2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl)methyl)piperazin-1-yl)benzoate

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Chemsigma International Co.,Ltd.

bulk?production Application:Pharmaceutical intermediates

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

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ZHEJIANG JIUZHOU CHEM CO.,LTD

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Methyl 2-[(1H-pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoate

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Amadis Chemical Co., Ltd.

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Methyl 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

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EnBridge PharmTech Co., Ltd.

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Methyl 2-[(1H-Pyrrolo[2,3-b]Pyridin-5-yl)oxy]-4-[4-[[2-(4-Chlorophenyl)-4,4-Dimethylcyclohex-1-enyl] Methyl]Piperazin-1-yl]Benzoate

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Toda Biotechnology Co., Limited.

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Methyl 2-[(1H-pyrrolo[2,3-b]pyridin-5-yl)oxy]-4-[4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl]methyl]piperazin-1-yl]benzoate,1235865-76-5

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Finetech Industry Limited

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Debye Scientific

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methyl 2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)-4-(4-((2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl)methyl)piperazin-1-yl)benzoate

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NovaChemistry

high purity Application:Drug intermediates Materials intermediates and active molecules

methyl 2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)-4-(4-((2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl)methyl)piperazin-1-yl)benzoate

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Synthetic route

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

: C16H21ClO3S

: 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

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; Inert atmosphere;	88%

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

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

: 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

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate In dimethyl sulfoxide at 140℃; for 12h; Inert atmosphere;	76%
With dipotassium hydrogenphosphate In dimethyl sulfoxide at 140℃; Inert atmosphere;	51%
With dipotassium hydrogenphosphate In dimethyl sulfoxide at 135℃; for 24h;

: C27H33ClN2O3

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

: 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

Conditions

Conditions	Yield
With copper(l) iodide; t-butyl malonate; caesium carbonate In dimethyl sulfoxide at 120℃; for 12h; Solvent; Reagent/catalyst; Inert atmosphere;	75%

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

: 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

Conditions

Conditions	Yield
Multi-step reaction with 4 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 View Scheme
Multi-step reaction with 4 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 View Scheme
Multi-step reaction with 4 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 View Scheme

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

: 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

Conditions

Conditions	Yield
Multi-step reaction with 3 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 View Scheme
Multi-step reaction with 3 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 View Scheme
Multi-step reaction with 3 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 View Scheme
Multi-step reaction with 3 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 View Scheme
Multi-step reaction with 3 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 View Scheme

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

: 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

Conditions

Conditions	Yield
Multi-step reaction with 6 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 View Scheme
Multi-step reaction with 6 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 View Scheme
Multi-step reaction with 6 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 View Scheme

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

: 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

Conditions

Conditions	Yield
Multi-step reaction with 5 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 View Scheme
Multi-step reaction with 5 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 View Scheme
Multi-step reaction with 5 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 View Scheme

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

: 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

Conditions

Conditions	Yield
Multi-step reaction with 4 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 View Scheme
Multi-step reaction with 4 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 View Scheme
Multi-step reaction with 4 steps 1.1: lithium borohydride; methanol / diethyl ether / 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 View Scheme

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

: 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

Conditions

Conditions	Yield
Multi-step reaction with 3 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 View Scheme
Multi-step reaction with 3 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 View Scheme
Multi-step reaction with 3 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 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

: 1235865-76-5
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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: trifluoroacetic acid; triethylsilane / dichloromethane / 1 h 2: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C View Scheme
Multi-step reaction with 2 steps 1: triethylsilane; trifluoroacetic acid / dichloromethane / 1 h 2: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C View Scheme
Multi-step reaction with 2 steps 1: triethylsilane; trifluoroacetic acid / dichloromethane / 1 h 2: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride / ethyl acetate; dichloromethane / 3 h / 0 - 20 °C 2: dipotassium hydrogenphosphate / dimethyl sulfoxide / 12 h / 140 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: trifluoroacetic acid; triethylsilane / dichloromethane / 1 h 2: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C View Scheme

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

: 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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium phosphate / diethylene glycol dimethyl ether / 24 h / 115 °C 2: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C View Scheme
Multi-step reaction with 2 steps 1: potassium phosphate / diethylene glycol dimethyl ether / 24 h / 115 °C 2: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C View Scheme
Multi-step reaction with 2 steps 1: potassium phosphate / diethylene glycol dimethyl ether / 24 h / 115 °C 2: dipotassium hydrogenphosphate / dimethyl sulfoxide / 24 h / 135 °C View Scheme

: 1679-18-1
4-Chlorophenylboronic acid

: 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

Conditions

Conditions	Yield
Multi-step reaction with 5 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 View Scheme

Yield

Multi-step reaction with 5 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
View Scheme

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

: 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

Conditions

Conditions	Yield
Multi-step reaction with 4 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 View Scheme

: C15H11N3O5

: 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

Conditions

Conditions	Yield
Multi-step reaction with 3 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 View Scheme

: C15H13N3O3

: 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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / tert-butyl alcohol / 48 h 2: potassium carbonate / N,N-dimethyl-formamide / 50 °C / Inert atmosphere View Scheme

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

: 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

Conditions

Conditions	Yield
Multi-step reaction with 4 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 View Scheme
Multi-step reaction with 2 steps 1: potassium phosphate heptahydrate / diethylene glycol dimethyl ether / 115 °C / Inert atmosphere 2: dipotassium hydrogenphosphate / dimethyl sulfoxide / 140 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 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 View Scheme
Multi-step reaction with 3 steps 1: potassium phosphate / diethylene glycol dimethyl ether / 110 °C 2: dimethyl sulfoxide / 2 h / 90 °C 3: triethylamine / tetrahydrofuran / 3 h / 67 °C View Scheme
Multi-step reaction with 2 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 View Scheme

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

: 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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium phosphate heptahydrate / diethylene glycol dimethyl ether / 115 °C / Inert atmosphere 2: dipotassium hydrogenphosphate / dimethyl sulfoxide / 140 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 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 View Scheme
Multi-step reaction with 3 steps 1: potassium phosphate / diethylene glycol dimethyl ether / 110 °C 2: dimethyl sulfoxide / 2 h / 90 °C 3: triethylamine / tetrahydrofuran / 3 h / 67 °C View Scheme
Multi-step reaction with 2 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 View Scheme

: 2979-19-3
3,3-dimethylcyclohexanone

: 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

Conditions

Conditions	Yield
Multi-step reaction with 6 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 View Scheme
Multi-step reaction with 5 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 View Scheme
Multi-step reaction with 8 steps 1.1: sodium hydride / tetrahydrofuran / 4 h / Inert atmosphere; Reflux 2.1: sodium hydride / dichloromethane / 0.5 h / 0 °C 2.2: -25 - 20 °C 3.1: tetrakis(triphenylphosphine) palladium(0); potassium fluoride / dichloromethane; methanol / 6 h / 65 °C / Inert atmosphere 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C 5.1: 1H-imidazole; triphenylphosphine; iodine / acetonitrile; diethyl ether / 1 h / -5 °C 6.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 80 °C 7.1: hydrogenchloride / ethyl acetate; dichloromethane / 3 h / 0 - 20 °C 8.1: dipotassium hydrogenphosphate / dimethyl sulfoxide / 12 h / 140 °C / Inert atmosphere View Scheme

: 1583-58-0
2,4-difluoro-benzoic acid

: 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

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium hydroxide / dimethyl sulfoxide / 8 h / 130 °C 2: thionyl chloride / 5 h / 60 °C 3: dimethyl sulfoxide / 5 h / 20 °C 4: sodium tris(acetoxy)borohydride / dichloromethane / 5 h / 30 °C 5: caesium carbonate; copper(l) iodide; t-butyl malonate / dimethyl sulfoxide / 12 h / 120 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: sulfuric acid / 8 h / 60 °C 2: potassium phosphate / diethylene glycol dimethyl ether / 110 °C 3: dimethyl sulfoxide / 2 h / 90 °C 4: triethylamine / tetrahydrofuran / 3 h / 67 °C View Scheme

: 345-29-9
4-fluorosalicylic acid

: 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

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride / 5 h / 60 °C 2: dimethyl sulfoxide / 5 h / 20 °C 3: sodium tris(acetoxy)borohydride / dichloromethane / 5 h / 30 °C 4: caesium carbonate; copper(l) iodide; t-butyl malonate / dimethyl sulfoxide / 12 h / 120 °C / Inert atmosphere View Scheme

: 392-04-1
methyl 4-fluoro-2-hydroxybenzoate

: 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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: dimethyl sulfoxide / 5 h / 20 °C 2: sodium tris(acetoxy)borohydride / dichloromethane / 5 h / 30 °C 3: caesium carbonate; copper(l) iodide; t-butyl malonate / dimethyl sulfoxide / 12 h / 120 °C / Inert atmosphere View Scheme

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

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

: 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

Conditions

Conditions	Yield
Stage #1: 4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-carbaldehyde; methyl 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(piperazin-1-yl)benzoate In tetrahydrofuran at 32℃; for 0.166667h; Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran at 5℃; for 20h;	48.2 mg

: 183208-36-8
5-methoxy-1H-pyrrolo[2,3-b]pyridine

: 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

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: boron tribromide / dichloromethane / 4 h / 0 - 27 °C 2: potassium phosphate / diethylene glycol dimethyl ether / 110 °C 3: dimethyl sulfoxide / 2 h / 90 °C 4: triethylamine / tetrahydrofuran / 3 h / 67 °C View Scheme

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

: 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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethyl sulfoxide / 2 h / 90 °C 2: triethylamine / tetrahydrofuran / 3 h / 67 °C View Scheme

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

: 1-(2-(bromomethyl)-5,5-dimethylcyclohex-1-enyl)-4-chlorobenzene

: 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

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 67℃; for 3h;	127 g

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

: 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

Conditions

Conditions	Yield
Multi-step reaction with 4 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 View Scheme

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

: 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

Conditions

Conditions	Yield
Multi-step reaction with 3 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 View Scheme

: 195062-61-4
4-chlorophenylboronic acid pinacol ester

: 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

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium fluoride / dichloromethane; methanol / 6 h / 65 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C 3: 1H-imidazole; triphenylphosphine; iodine / acetonitrile; diethyl ether / 1 h / -5 °C 4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 80 °C 5: hydrogenchloride / ethyl acetate; dichloromethane / 3 h / 0 - 20 °C 6: dipotassium hydrogenphosphate / dimethyl sulfoxide / 12 h / 140 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 6 steps
1: tetrakis(triphenylphosphine) palladium(0); potassium fluoride / dichloromethane; methanol / 6 h / 65 °C / Inert atmosphere
2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C
3: 1H-imidazole; triphenylphosphine; iodine / acetonitrile; diethyl ether / 1 h / -5 °C
4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 80 °C
5: hydrogenchloride / ethyl acetate; dichloromethane / 3 h / 0 - 20 °C
6: dipotassium hydrogenphosphate / dimethyl sulfoxide / 12 h / 140 °C / Inert atmosphere
View Scheme

: 4'-chloro-6-(iodomethyl)-3,3-dimethyl-2,3,4,5-tetrahydro-1,1'-biphenyl

: 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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 80 °C 2: hydrogenchloride / ethyl acetate; dichloromethane / 3 h / 0 - 20 °C 3: dipotassium hydrogenphosphate / dimethyl sulfoxide / 12 h / 140 °C / Inert atmosphere View Scheme

: 637-87-6
1-Chloro-4-iodobenzene

: 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

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / dimethyl sulfoxide / 10 h / 95 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); potassium fluoride / dichloromethane; methanol / 6 h / 65 °C / Inert atmosphere 3: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C 4: 1H-imidazole; triphenylphosphine; iodine / acetonitrile; diethyl ether / 1 h / -5 °C 5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 80 °C 6: hydrogenchloride / ethyl acetate; dichloromethane / 3 h / 0 - 20 °C 7: dipotassium hydrogenphosphate / dimethyl sulfoxide / 12 h / 140 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 7 steps
1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / dimethyl sulfoxide / 10 h / 95 °C / Inert atmosphere
2: tetrakis(triphenylphosphine) palladium(0); potassium fluoride / dichloromethane; methanol / 6 h / 65 °C / Inert atmosphere
3: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C
4: 1H-imidazole; triphenylphosphine; iodine / acetonitrile; diethyl ether / 1 h / -5 °C
5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 80 °C
6: hydrogenchloride / ethyl acetate; dichloromethane / 3 h / 0 - 20 °C
7: dipotassium hydrogenphosphate / dimethyl sulfoxide / 12 h / 140 °C / Inert atmosphere
View Scheme

: 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%

: 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

: 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
Multi-step reaction with 2 steps 1.1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C 1.2: Cooling 2.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 24 h View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C 2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C 2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 24 h View Scheme

: 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

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C 1.2: Cooling 2.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane View Scheme

: 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

: {5-[5-(4-{[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-en-1-yl]methyl}piperazin-1-yl)-2-{[(4-{[(trans-4-methoxycyclohexyl)methyl]amino}-3-nitrophenyl)sulfonyl]carbamoyl}phenoxy]-7H-pyrrolo[2,3-b]pyridin-7-yl}methyl dihydrogen phosphate trifluoroacetate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C 1.2: Cooling 2.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane 3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 1.5 h / 80 °C / microwave irradiation 4.1: dichloromethane / 1 h View Scheme

: 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

: C56H73ClN7O11PS

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C 1.2: Cooling 2.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane 3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 1.5 h / 80 °C / microwave irradiation View Scheme

: 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

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C 2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C 3: hydrogenchloride / acetonitrile; water View Scheme

: 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

: 1379647-80-9
4-(4-{[2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-en-1-yl]methyl}piperazin-1-yl)-N-({3-nitro-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}sulfonyl)-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzamide sulfate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / 1,4-dioxane / 24 h / 50 °C 2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C 3: sulfuric acid / isopropyl alcohol / 70 °C View Scheme

: 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

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide; water / 1,4-dioxane / 24 h / 50 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane 2.2: 1.5 h View Scheme

: 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

: 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)-N-((3-nitro-4-(3-((tetrahydro-2H-pyran-4-yl)oxy)prop-1-yn-1-yl)phenyl)sulfonyl)benzamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / tetrahydrofuran; methanol; water / 45 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 20 °C 3: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / N,N-dimethyl-formamide / 60 °C View Scheme

: 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

: 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-((2-(tetrahydro-2H-pyran-4-yl)-2-azaspiro[3.3]heptan-6-yl)oxy)phenyl)sulfonyl)benzamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide / tetrahydrofuran; methanol; water / 45 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 16 h / 20 °C 3: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 4: sodium tris(acetoxy)borohydride / methanol; dichloromethane / 0.25 h / 20 °C View Scheme

: 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

: C50H57ClN8O7S

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium hydroxide / tetrahydrofuran; methanol; water / 45 °C 2: trichlorophosphate / 5 h / 85 °C 3: triethylamine / tetrahydrofuran / 20 °C 4: trifluoroacetic acid / dichloromethane / 20 °C 5: sodium tris(acetoxy)borohydride; sodium acetate / methanol; dichloromethane / 20 °C View Scheme

: 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

: 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
Multi-step reaction with 2 steps 1: sodium hydroxide / tetrahydrofuran; methanol; water / 45 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 16 h / 20 °C View Scheme

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