Dayangchem's R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. DayangChem can provide different quantities
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inquiryWelcome to Simagchem, your partner in China as a premier supply of bulk specialty chemicals for industry and life science. We introduce experienced quality product and exceptional JIT service with instant market intelligence in China to benefit our
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inquiryOur main production base is located in Xuzhou industry park. We are certified both to the ISO 9001 and ISO 14001 Standards, have a safety management system in place.Our R&D team masters core technology for process-design of target building block
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inquiryWith our good experience, we offer detailed technical support and advice to assist customers. We communicate closely with customers to establish their quality requirements. Consistent Quality Our plant has strict quality control in each manufacturin
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inquiryWITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et
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inquiry1. Guaranteed purity; 2. Large quantity in stock; 3. Largest manufacturer; 4. Best service after shipment with email; 5. High quality & competitive price; Appearance:powder Storage:Store in sealed containers at cool & dry pla
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inquiry1.No Less 8 years exporting experience. Clients can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specialized
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inquiryBest quality & Attractive price & Professional service; Trial & Pilot & Commercial Hisunny Chemical is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality intermediates, specia
Our company has been in existence for 10 years since its establishment. We have our own unique team. The company integrates independent research and development, production and sales. We have established famous brands at home and abroad. At present
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inquiryA substitute for perfluorooctanoic acid, mainly used as a surfactant, dispersant, additive, etc Appearance:White solid or Colorless liquid Purity:99.3 % We will ship the goods in a timely manner as required We can provide relevant documents acc
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inquiryThe above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi
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inquiryJ&H CHEM R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. J&H CHEM has some Manufacturing base in Jia
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inquiryOur company was built in 2009 with an ISO certificate.In the past 6 years, we have grown up as a famous fine chemicals supplier in China and we had established stable business relationships with Samsung,LG,Merck,Thermo Fisher Scientific and so
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inquiry1,3-Dibromo-5-fluoro-2-iodobenzene Basic information Product Name: 1,3-Dibromo-5-fluoro-2-iodobenzene Synonyms: 1,3-DIBROMO-5-FLUORO-2-IODOBENZENE;2,6-DIBROMO-4-FLUOROIODOBENZENE;2,6-Dibromo-4-fluoroiodobenzene 97%;2,6-Dibromo-4-fluoroiodobenz
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inquiryZhenyu biotech exported this product to many countries and regions at best price. if you are looking for the material's manufacturer or supplier in china, zhenyu biotech is your best choice. pls contact with us freely for getting detailed
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inquiryAppearance:95%+ Package:R&D,Pilot run Transportation:per client require Port:Express ,Air, Sea
High quality,stable supply chain.Appearance:white/off-white or light yellow Storage:Store in cool and dry place, keep away from strong light and heat. Package:aluminum bottle,glass bottle,PTFE bottle,cardboard drum Application:This product can be use
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inquiryGOLDEN PHARMA CO.,LIMITED.is a professional pharmaceutical company,our team have more than 20years expereince in pharmaceutical production and sales. we are a professional technical enterprise specializing in the R & D, production,QA regulation
Stock products, own laboratory Package:Grams, Kilograms Application:For R&D Transportation:According to customer request Port:Shanghai
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inquiryLower price, sample is available,SDS test documents are available,large stock in warehouseAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:Fine chemical intermediates, used as the main raw material for the synthe
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inquiryhigh purity lowest priceAppearance:solid or liquid Storage:in sealed air resistant place Package:drum and bag Application:for pharma use Transportation:by sea or air Port:Beijing or Guangzhou
R & D enterprises have their own stock in stockAppearance:To be subject to the object Package:Customized Application:pharmaceutical intermediates Transportation:Air Port:Shanghai;Guangzhou
Shanghai Lonwin Chemical company is a subsidiary of Lonwin Industry Group Limited, was established in 2011 and is headquartered in Shanghai, adjacent to China National Convention and Exhibition Center and Hongqiao transportation hub.Lonwinchem is
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inquiryQ1: Are you a manufacturer Answer: Yes, we are factory founded on 2012.Q2: How to contact with us Click "contact supplier" And then send us message the product you interest in, you will get reply within 12 hours.Q3:Which kind of payment terms do you
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inquiryAcmec is a leading manufacturer and supplier of biochemical reagents and life science products. We have over 40,000 items in stock (real-time inventory) and offer discounted prices to registered members of the online store ( www.acmec.com.cn ) Appea
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inquiryhigh quality Storage:Sealed, dry, microtherm , avoid light and smell. Package:According to the demand of customer Application:Organic synthesis Transportation:by air or by sea
Our clients, like BASF,CHEMO,Brenntag,ASR,Evonik,Merck and etc.Appearance:COA Storage:in stock Application:MSDS/TDS
Ansciep Chemical is a professional enterprise manufacturing and distributing fine chemicals and speciality chemicals. We have been dedicated to heterocycle compounds and phenyl rings for tens of years. This is our mature product for export. Our quali
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inquiryAmoychem is committed to providing the top-quality chemical products and services Internationally. We offer our customers with friendly, professional service and reliable, high performance products that have been manufactured according to the accredi
★.Best quality according to requirement ★.Competitive price in China market ★.Mature Technical support ★.Professional logistic support
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inquiryC10H12Br2FN3
1,3-dibromo-2-iodo-5-fluorobenzene
Conditions | Yield |
---|---|
With hydrogen iodide In acetonitrile at 60℃; for 1.5h; | 71% |
2,6-dibromo-4-fluoroaniline
1,3-dibromo-2-iodo-5-fluorobenzene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 98 percent / i-pentyl nitrite; HOAc / 0 - 5 °C 2: 95 percent / aq. NaOH / 0.5 h / 0 - 5 °C 3: 71 percent / aq. HI / acetonitrile / 1.5 h / 60 °C View Scheme |
1,3-dibromo-2-iodo-5-fluorobenzene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 95 percent / aq. NaOH / 0.5 h / 0 - 5 °C 2: 71 percent / aq. HI / acetonitrile / 1.5 h / 60 °C View Scheme |
1,3-dibromo-2-iodo-5-fluorobenzene
prenyl bromide
Conditions | Yield |
---|---|
Stage #1: 1,3-dibromo-5-fluoro-2-iodobenzene With isopropylmagnesium chloride In tetrahydrofuran at -20 - 0℃; for 1h; Inert atmosphere; Stage #2: prenyl bromide With copper(l) iodide In tetrahydrofuran at 0 - 20℃; | 85% |
1,3-dibromo-2-iodo-5-fluorobenzene
thioacetic acid S-(2-acetylamino-phenyl)ester
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 130℃; for 10h; Inert atmosphere; | 65% |
1,3-dibromo-2-iodo-5-fluorobenzene
phenylboronic acid
2,6-dibromo-4-fluorobiphenyl
Conditions | Yield |
---|---|
Stage #1: 1,3-dibromo-5-fluoro-2-iodobenzene With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride; potassium carbonate In 1,4-dioxane at 20℃; for 1h; Suzuki-Miyaura coupling; Inert atmosphere; Stage #2: phenylboronic acid In 1,4-dioxane for 36h; Suzuki-Miyaura coupling; Inert atmosphere; Reflux; | 58% |
1,3-dibromo-2-iodo-5-fluorobenzene
N,N-dimethyl-formamide
2,6-dibromo-4-fluorobenzaldehyde
Conditions | Yield |
---|---|
Stage #1: 1,3-dibromo-5-fluoro-2-iodobenzene With isopropylmagnesium chloride In diethyl ether; toluene at -35 - -25℃; for 2h; Stage #2: N,N-dimethyl-formamide In diethyl ether; toluene at -19 - 10℃; for 2h; Product distribution / selectivity; | 54% |
Stage #1: 1,3-dibromo-5-fluoro-2-iodobenzene With isopropylmagnesium chloride In diethyl ether; toluene at -35 - -25℃; for 2h; Stage #2: N,N-dimethyl-formamide In diethyl ether; toluene at -19 - 10℃; for 2h; | 54% |
Stage #1: 1,3-dibromo-5-fluoro-2-iodobenzene With isopropylmagnesium chloride In ethyl acetate; toluene at -35 - -25℃; for 2h; Stage #2: N,N-dimethyl-formamide In ethyl acetate; toluene at 10 - 20℃; for 3h; | 54% |
Stage #1: 1,3-dibromo-5-fluoro-2-iodobenzene With isopropylmagnesium chloride In diethyl ether; toluene at -35 - -25℃; for 1.5h; Stage #2: N,N-dimethyl-formamide In diethyl ether; toluene at -19 - 10℃; for 1.5h; | 54% |
Stage #1: 1,3-dibromo-5-fluoro-2-iodobenzene With isopropylmagnesium chloride In tetrahydrofuran; toluene at -35 - -25℃; for 2h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; toluene at -35 - 20℃; for 1.5h; | 49% |
1,3-dibromo-2-iodo-5-fluorobenzene
isopropylmagnesium chloride
N,N-dimethyl-formamide
2,6-dibromo-4-fluorobenzaldehyde
Conditions | Yield |
---|---|
Stage #1: 1,3-dibromo-5-fluoro-2-iodobenzene; isopropylmagnesium chloride In diethyl ether; toluene at -35 - -25℃; for 2h; Stage #2: N,N-dimethyl-formamide In diethyl ether; toluene at -19 - 10℃; for 3h; | 54% |
1,3-dibromo-2-iodo-5-fluorobenzene
1,3-dibromo-5-fluorobenzene
Conditions | Yield |
---|---|
With isopropylmagnesium chloride In tetrahydrofuran; toluene at -35 - -25℃; for 2h; Inert atmosphere; |
1,3-dibromo-2-iodo-5-fluorobenzene
N,N-dimethyl-formamide
A
2,6-dibromo-4-fluorobenzaldehyde
B
1,3-dibromo-5-fluorobenzene
Conditions | Yield |
---|---|
Stage #1: 1,3-dibromo-5-fluoro-2-iodobenzene With isopropylmagnesium chloride In tetrahydrofuran Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; water Inert atmosphere; |
1,3-dibromo-2-iodo-5-fluorobenzene
2-(7,7-dimethyl-1-oxo-3,4,7,8-tetrahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-2(6H)-yl)-4-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: triethylamine / dichloromethane / 16 h / 20 °C 4.1: caesium carbonate / 1,4-dioxane / 0.5 h / Sealed tube 4.2: 16 h / 100 °C 5.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / dichloromethane; 1,4-dioxane / 5 h / 100 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C 4.1: caesium carbonate / 1,4-dioxane / 0.5 h / Sealed tube 4.2: 16 h / 100 °C 5.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / dichloromethane; 1,4-dioxane / 5 h / 100 °C View Scheme |
1,3-dibromo-2-iodo-5-fluorobenzene
(2,6-dibromo-4-fluorophenyl)methanol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C View Scheme | |
Multi-step reaction with 3 steps 1: hydrogenchloride / toluene; diethyl ether / 2 h / -35 - -25 °C 2: toluene; diethyl ether / 3 h / -25 - 10 °C 3: sodium tetrahydroborate / ethanol / 4 h / 10 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: diethyl ether; toluene / 2 h / -35 - -25 °C 1.2: 3 h / -19 - 10 °C 2.1: sodium tetrahydroborate / ethanol / 4 h / 10 °C View Scheme |
1,3-dibromo-2-iodo-5-fluorobenzene
2-bromo-4-fluoro-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: triethylamine / dichloromethane / 16 h / 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 5 steps 1: hydrogenchloride / toluene; diethyl ether / 2 h / -35 - -25 °C 2: toluene; diethyl ether / 3 h / -25 - 10 °C 3: sodium tetrahydroborate / ethanol / 4 h / 10 °C 4: pyridine / dichloromethane / 5 h / 0 - 20 °C 5: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1.1: diethyl ether; toluene / 2 h / -35 - -25 °C 1.2: 3 h / -19 - 10 °C 2.1: sodium tetrahydroborate / ethanol / 4 h / 10 °C 3.1: triethylamine / dichloromethane / 16 h / 10 °C / Inert atmosphere 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere View Scheme |
1,3-dibromo-2-iodo-5-fluorobenzene
4-Fluoro-2-(1-oxo-3,4,6,7,8,9-hexahydro-pyrazino[1,2-a]indol-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: triethylamine / dichloromethane / 16 h / 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 5 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 6 steps 1: hydrogenchloride / toluene; diethyl ether / 2 h / -35 - -25 °C 2: toluene; diethyl ether / 3 h / -25 - 10 °C 3: sodium tetrahydroborate / ethanol / 4 h / 10 °C 4: pyridine / dichloromethane / 5 h / 0 - 20 °C 5: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 6: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 5 steps 1.1: diethyl ether; toluene / 2 h / -35 - -25 °C 1.2: 3 h / -19 - 10 °C 2.1: sodium tetrahydroborate / ethanol / 4 h / 10 °C 3.1: triethylamine / dichloromethane / 16 h / 10 °C / Inert atmosphere 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere View Scheme |
1,3-dibromo-2-iodo-5-fluorobenzene
(S)-2-(5-(5-(2-ethyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4-fluoro-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: triethylamine / dichloromethane / 16 h / 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere 6.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 1 h / 100 °C / Sealed tube View Scheme | |
Multi-step reaction with 6 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere 6.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 1 h / 100 °C / Sealed tube View Scheme |
1,3-dibromo-2-iodo-5-fluorobenzene
(S)-2-(3-(5-(5-(2-ethyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-5-fluoro-2-(hydroxymethyl)phenyl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: triethylamine / dichloromethane / 16 h / 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere 6.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 1 h / 100 °C / Sealed tube 7.1: lithium hydroxide; water / isopropyl alcohol; tetrahydrofuran / 1 h / 30 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere 6.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 1 h / 100 °C / Sealed tube 7.1: lithium hydroxide; water / isopropyl alcohol; tetrahydrofuran / 1 h / 30 °C View Scheme |
1,3-dibromo-2-iodo-5-fluorobenzene
(S)-4-fluoro-2-(1-methyl-5-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: triethylamine / dichloromethane / 16 h / 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere 6.1: sodium acetate; potassium phosphate tribasic trihydrate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 2 h / 110 °C / Sealed tube; Inert atmosphere View Scheme | |
Multi-step reaction with 6 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere 6.1: sodium acetate; potassium phosphate tribasic trihydrate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 2 h / 110 °C / Sealed tube; Inert atmosphere View Scheme |
1,3-dibromo-2-iodo-5-fluorobenzene
(S)-2-(5-fluoro-2-(hydroxymethyl)-3-(1-methyl-5-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)phenyl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: triethylamine / dichloromethane / 16 h / 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere 6.1: sodium acetate; potassium phosphate tribasic trihydrate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 2 h / 110 °C / Sealed tube; Inert atmosphere 7.1: lithium hydroxide; water / isopropyl alcohol; tetrahydrofuran / 0.5 h View Scheme | |
Multi-step reaction with 7 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere 6.1: sodium acetate; potassium phosphate tribasic trihydrate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 2 h / 110 °C / Sealed tube; Inert atmosphere 7.1: lithium hydroxide; water / isopropyl alcohol; tetrahydrofuran / 0.5 h View Scheme |
1,3-dibromo-2-iodo-5-fluorobenzene
(R)-2-(5-(5-(3,4-Dimethylpiperazin-1-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4-fluoro-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: triethylamine / dichloromethane / 16 h / 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere 6.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 2 h / 110 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere 6.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 2 h / 110 °C View Scheme |
1,3-dibromo-2-iodo-5-fluorobenzene
(R)-2-(5-((5-(2,4-dimethylpiperazin-1-yl)pyridin-2-yl)amino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4-fluoro-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: triethylamine / dichloromethane / 16 h / 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere 6.1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 2 h / 100 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere 6.1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 2 h / 100 °C View Scheme |
1,3-dibromo-2-iodo-5-fluorobenzene
4-fluoro-2-(5-(5-(3-(fluoromethyl)-4-methylpiperazin-1-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-6-(1-oxo-3,4,6,7,8,9-hexa-hydropyrazino[1,2-a]indol-2(1H)-yl)benzyl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: triethylamine / dichloromethane / 16 h / 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere 6.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 3 h / 110 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere 6.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 3 h / 110 °C View Scheme |
1,3-dibromo-2-iodo-5-fluorobenzene
2-(5-fluoro-3-(5-(5-(3-(fluoromethyl)-4-methylpiperazin-1-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-(hydroxymethyl)phenyl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: triethylamine / dichloromethane / 16 h / 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere 6.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 3 h / 110 °C 7.1: lithium hydroxide monohydrate / water; isopropyl alcohol; tetrahydrofuran / 1 h / 30 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere 6.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 3 h / 110 °C 7.1: lithium hydroxide monohydrate / water; isopropyl alcohol; tetrahydrofuran / 1 h / 30 °C View Scheme |
1,3-dibromo-2-iodo-5-fluorobenzene
4-fluoro-2-(1-methyl-5-(5-(9-methyl-7-oxa-3,9-diaza-bicyclo-[3.3.1]nonan-3-yl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: triethylamine / dichloromethane / 16 h / 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere 6.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 3 h / 110 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere 6.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 3 h / 110 °C View Scheme |
1,3-dibromo-2-iodo-5-fluorobenzene
2-bromo-6-(7,7-difluoro-1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)-4-fluorobenzyl Acetate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: triethylamine / dichloromethane / 16 h / 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere View Scheme |
1,3-dibromo-2-iodo-5-fluorobenzene
(S)-2-(7,7-difluoro-1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)-4-fluoro-6-(1-methyl-5-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)benzyl Acetate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: triethylamine / dichloromethane / 16 h / 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 1 h / 100 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 1 h / 100 °C View Scheme |
1,3-dibromo-2-iodo-5-fluorobenzene
(S)-7,7-difluoro-2-(5-fluoro-2-(hydroxymethyl)-3-(1-methyl-5-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)phenyl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: triethylamine / dichloromethane / 16 h / 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 1 h / 100 °C 6.1: lithium hydroxide / water; isopropyl alcohol; tetrahydrofuran / 1 h / 30 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5.1: sodium acetate; potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile; water / 1 h / 100 °C 6.1: lithium hydroxide / water; isopropyl alcohol; tetrahydrofuran / 1 h / 30 °C View Scheme |
1,3-dibromo-2-iodo-5-fluorobenzene
2,6-dibromo-4-fluorobenzyl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: triethylamine / dichloromethane / 16 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: hydrogenchloride / toluene; diethyl ether / 2 h / -35 - -25 °C 2: toluene; diethyl ether / 3 h / -25 - 10 °C 3: sodium tetrahydroborate / ethanol / 4 h / 10 °C 4: pyridine / dichloromethane / 5 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: diethyl ether; toluene / 2 h / -35 - -25 °C 1.2: 3 h / -19 - 10 °C 2.1: sodium tetrahydroborate / ethanol / 4 h / 10 °C 3.1: triethylamine / dichloromethane / 16 h / 10 °C / Inert atmosphere View Scheme |
1,3-dibromo-2-iodo-5-fluorobenzene
(S)-2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-fluoro-6-(1-methyl-5-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)benzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: isopropylmagnesium chloride / toluene; diethyl ether / 1.5 h / -35 - -25 °C 1.2: 1.5 h / -19 - 10 °C 2.1: potassium acetate; 4,7-dimethoxy-1,10-phenanthroline; copper(l) iodide / 1,4-dioxane / 10 h / 90 °C / Inert atmosphere 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate; potassium phosphate / tetrahydrofuran; water / 2 h / 100 °C / Inert atmosphere View Scheme |
1,3-dibromo-2-iodo-5-fluorobenzene
(2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}-6-[5-({5-[(2S)-2-ethyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl}amino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl]-4-fluorophenyl)methyl Acetate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: triethylamine / dichloromethane / 16 h / 20 °C 4.1: caesium carbonate / 1,4-dioxane / 0.5 h / Sealed tube 4.2: 16 h / 100 °C 5.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / dichloromethane; 1,4-dioxane / 5 h / 100 °C 6.1: sodium acetate; potassium phosphate / acetonitrile; water / 2 h / Reflux View Scheme | |
Multi-step reaction with 6 steps 1.1: isopropylmagnesium chloride / toluene; ethyl acetate / 2 h / -35 - -25 °C 1.2: 3 h / 10 - 20 °C 2.1: sodium tetrahydroborate; ethanol / 4 h / 10 °C 3.1: pyridine / dichloromethane / 5 h / 0 - 20 °C 4.1: caesium carbonate / 1,4-dioxane / 0.5 h / Sealed tube 4.2: 16 h / 100 °C 5.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / dichloromethane; 1,4-dioxane / 5 h / 100 °C 6.1: sodium acetate; potassium phosphate / acetonitrile; water / 2 h / Reflux View Scheme |
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