3,10-dibromo-8-chloro-5,6-dihydro-11H-benzo<5,6>cyclohepta<1,2-b>pyridin-11-one

Base Information

• Chemical Name: 3,10-dibromo-8-chloro-5,6-dihydro-11H-benzo<5,6>cyclohepta<1,2-b>pyridin-11-one
• CAS No.: 193276-55-0
• Molecular Formula: C₁₄H₈Br₂ClNO
• Molecular Weight: 401.485
• Mol file: 193276-55-0.mol

Synonyms:3,10-dibromo-8-chloro-5,6-dihydro-11H-benzo<5,6>cyclohepta<1,2-b>pyridin-11-one

Chemical Property of 3,10-dibromo-8-chloro-5,6-dihydro-11H-benzo<5,6>cyclohepta<1,2-b>pyridin-11-one

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3,10-dibromo-8-chloro-5,6-dihydro-11H-benzo<5,6>cyclohepta<1,2-b>pyridin-11-one

There total 1 articles about 3,10-dibromo-8-chloro-5,6-dihydro-11H-benzo<5,6>cyclohepta<1,2-b>pyridin-11-one 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:

5-bromo-3-[2-(3-bromo-5-chloro-2-iodo-phenyl)-ethyl]-pyridine-2-carboxylic acid methyl-phenyl-amide (213771-69-8) → 3,10-dibromo-8-chloro-5,6-dihydro-11H-benzo<5,6>cyclohepta<1,2-b>pyridin-11-one (193276-55-0) + 5-bromo-3-[2-(3-bromo-5-chloro-phenyl)-ethyl]-pyridine-2-carboxylic acid methyl-phenyl-amide

Guidance literature:

With (2,4,6-trimethoxyphenyl)magnesium bromide; at -20 ℃; for 8h; Further Variations:; Temperatures; Reagents; times; Product distribution;

DOI:10.1021/ol016809d

Reference yield: 84.0%

3,10-dibromo-8-chloro-5,6-dihydro-11H-benzo<5,6>cyclohepta<1,2-b>pyridin-11-one (193276-55-0) → 8-chloro-3,10-dibromo-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridine (272107-22-9)

Guidance literature:

With acetic anhydride; trifluoroacetic acid; zinc; In tetrahydrofuran; at -25 - 18 ℃; for 24h;

DOI:10.1021/jo034380t

Reference yield:

3,10-dibromo-8-chloro-5,6-dihydro-11H-benzo<5,6>cyclohepta<1,2-b>pyridin-11-one (193276-55-0) → lonafarnib (193275-84-2,193275-86-4,193275-85-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 84 percent / zinc dust; acetic anhydride; trifluoroacetic acid / tetrahydrofuran / 24 h / -25 - 18 °C

2.1: lithium diisopropylamide*THF; quinine; water / toluene; cyclohexane / 21 h / 5 - 25 °C

2.2: 10.5 g / sulfuric acid / toluene / 4 h / 85 °C

3.1: 80 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide; toluene / 18 h / 20 °C

4.1: hydrochloric acid / ethanol / 6 h / 20 °C

5.1: 5.44 g / NaOH / ethanol; 1-methyl-pyrrolidin-2-one / 10 h / 110 °C / pH 9

With hydrogenchloride; sodium hydroxide; water; acetic anhydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; zinc; lithium diisopropyl amide; Quinine; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; ethanol; cyclohexane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo034380t

upstream raw materials:

5-bromo-3-[2-(3-bromo-5-chloro-2-iodo-phenyl)-ethyl]-pyridine-2-carboxylic acid methyl-phenyl-amide

Downstream raw materials:

8-chloro-3,10-dibromo-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridine

(R)-(+)-(8-chloro-3,10-dibromo-6,11-dihydro-5H-benzo-<5,6>cyclohepta<1,2-b>pyridin-11-yl)-1-piperidine

lonafarnib