Tert-butyl 3-bromo-6-chloropicolinate

Base Information

• Chemical Name: Tert-butyl 3-bromo-6-chloropicolinate
• CAS No.: 1235036-15-3
• Molecular Formula: C10H11BrClNO2
• Molecular Weight: 292.56
• Hs Code.: 2933399090
• Mol file: 1235036-15-3.mol

Synonyms:Tert-butyl 3-bromo-6-chloropicolinate;2-Pyridinecarboxylic acid, 3-broMo-6-chloro-, 1,1-diMethylethyl ester

Chemical Property of Tert-butyl 3-bromo-6-chloropicolinate

Chemical Property:

• Boiling Point: 334.3±37.0 °C(Predicted)
• PKA: -3.48±0.10(Predicted)
• PSA: 39.19000
• Density: 1.475±0.06 g/cm3(Predicted)
• LogP: 3.45280
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,?1-?DimethylethylEster3-?Bromo-?6-?chloro-?2-?PyridinecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1,?1-?Dimethylethyl Ester 3-?Bromo-?6-?chloro-?2-?Pyridinecarboxylic Acid was used to study expeditious synthesis of isoquinolones and isocoumarins.

Technology Process of Tert-butyl 3-bromo-6-chloropicolinate

There total 1 articles about Tert-butyl 3-bromo-6-chloropicolinate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

3-bromo-6-chloropyridine-2-carboxylic acid (929000-66-8) + tert-butyl alcohol (75-65-0) → tert-butyl 3-bromo-6-chloropicolinate (1235036-15-3)

Guidance literature:

With pyridine; p-toluenesulfonyl chloride; at 0 - 12 ℃; for 12h;

Reference yield:

tert-butyl 3-bromo-6-chloropicolinate (1235036-15-3) → 6-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-phenylpropyl)picolinic acid

Guidance literature:

Multi-step reaction with 3 steps

1: caesium carbonate / N,N-dimethyl-formamide / 12 h / 120 °C

2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / tetrahydrofuran / 0.5 h / 100 °C / Microwave irradiation

3: trifluoroacetic acid / dichloromethane

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

tert-butyl 3-bromo-6-chloropicolinate (1235036-15-3) → 6-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-phenethylpicolinic acid

Guidance literature:

Multi-step reaction with 3 steps

1.1: caesium carbonate / 12 h / 120 °C / Inert atmosphere; Molecular sieve

2.1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate / tetrahydrofuran / 0.08 h

2.2: 28 h

3.1: lithium hydroxide / water; ethanol / 16 h / 60 °C

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; caesium carbonate; lithium hydroxide; In tetrahydrofuran; ethanol; water;

DOI:10.1021/ml500030p

upstream raw materials:

3-bromo-6-chloropyridine-2-carboxylic acid

tert-butyl alcohol

Downstream raw materials:

tert-butyl 6-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-(4-methyl-3-phenoxyphenyl)picolinate

6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl]-3-[3-(cyclohexylmethoxy)-2-methylphenyl]pyridine-2-carboxylic acid tert-butyl ester

6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl]-3-(1-benzyl-1H-1,2,3-triazol-4-yl)pyridine-2-carboxylic acid

tert-butyl 6-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-(1-benzyl-1H-1,2,3-triazol-4-yl)picolinate

Refernces

• 1、 Koehler, Michael F. T.,Bergeron, Philippe,Choo, Edna F.,Lau, Kevin,Ndubaku, Chudi,Dudley, Danette,Gibbons, Paul,Sleebs, Brad E.,Rye, Carl S.,Nikolakopoulos, George,Bui, Chinh,Kulasegaram, Sanji,Kersten, Wilhelmus J. A.,Smith, Brian J.,Czabotar, Peter E.,Colman, Peter M.,Huang, David C. S.,Baell, Jonathan B.,Watson, Keith G.,Hasvold, Lisa,Tao, Zhi-Fu,Wang, Le,Souers, Andrew J.,Elmore, Steven W.,Flygare, John A.,Fairbrother, Wayne J.,Lessene, Guillaume. "Structure-guided rescaffolding of selective antagonists of BCL-X L". supporting information. p. 662 - 667. Retrieved 2014/07/07.
• 2、 -. "APOPTOSIS-INDUCING AGENTS FOR THE TREATMENT OF CANCER AND IMMUNE AND AUTOIMMUNE DISEASES". Paragraph 1224. . Retrieved 2013/04/24.