(6S,12aR)-3,10-dibromo-6-phenyl-12,12a-dihydro-6H-benzo[5,6][1,3]oxazino[3,4-a]indole

Base Information

• Chemical Name: (6S,12aR)-3,10-dibromo-6-phenyl-12,12a-dihydro-6H-benzo[5,6][1,3]oxazino[3,4-a]indole
• CAS No.: 1585969-16-9
• Molecular Formula: C₂₁H₁₅Br₂NO
• Molecular Weight: 457.164
• Mol file: 1585969-16-9.mol

Synonyms:(6S,12aR)-3,10-dibromo-6-phenyl-12,12a-dihydro-6H-benzo-[5,6][1,3]oxazino[3,4-a]indole

Chemical Property of (6S,12aR)-3,10-dibromo-6-phenyl-12,12a-dihydro-6H-benzo[5,6][1,3]oxazino[3,4-a]indole

Chemical Property:

• Boiling Point: 539.9±50.0 °C(Predicted)
• PKA: 1.47±0.40(Predicted)
• Density: 1.75±0.1 g/cm3(Predicted)

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (6S,12aR)-3,10-dibromo-6-phenyl-12,12a-dihydro-6H-benzo[5,6][1,3]oxazino[3,4-a]indole

There total 11 articles about (6S,12aR)-3,10-dibromo-6-phenyl-12,12a-dihydro-6H-benzo[5,6][1,3]oxazino[3,4-a]indole 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: 93.0%

(R)-5-bromo-2-(5-bromoindolin-2-yl)phenol (1585969-17-0,1954693-13-0) + benzaldehyde (100-52-7) → (6S,12aR)-3,10-dibromo-6-phenyl-12,12a-dihydro-6H-benzo-[5,6][1,3]oxazino[3,4-a]indole (1585969-16-9)

Guidance literature:

With trifluoroacetic acid; In acetonitrile; at 30 - 35 ℃; for 3h; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol500971c

Reference yield:

5-bromo-2-(2-(2,5-dibromophenyl)-1-iminoethyl)phenol (1585969-22-7) → (6S,12aR)-3,10-dibromo-6-phenyl-12,12a-dihydro-6H-benzo-[5,6][1,3]oxazino[3,4-a]indole (1585969-16-9)

Guidance literature:

Multi-step reaction with 3 steps

1: N-[(1R,2R)-1,2-diphenyl-2-(3-phenylpropylamino)ethyl]-4-methylbenzene sulfonamide ammonium chloride ruthenium; ammonium formate / dichloromethane / 24 h / 70 °C / 2016.93 Torr / Inert atmosphere

2: copper(l) iodide; caesium carbonate / N,N-dimethyl-formamide / 1 h / 45 °C / Inert atmosphere

3: trifluoroacetic acid / acetonitrile / 3 h / 30 - 35 °C / Inert atmosphere

With copper(l) iodide; N-[(1R,2R)-1,2-diphenyl-2-(3-phenylpropylamino)ethyl]-4-methylbenzene sulfonamide ammonium chloride ruthenium; ammonium formate; caesium carbonate; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ol500971c

Reference yield:

1-(4-bromo-2-hydroxyphenyl)-2-(2,5-dibromophenyl)ethanone (1403991-85-4) → (6S,12aR)-3,10-dibromo-6-phenyl-12,12a-dihydro-6H-benzo-[5,6][1,3]oxazino[3,4-a]indole (1585969-16-9)

Guidance literature:

Multi-step reaction with 4 steps

1: ammonia / methanol / 20 h / 20 °C / Inert atmosphere

2: N-[(1R,2R)-1,2-diphenyl-2-(3-phenylpropylamino)ethyl]-4-methylbenzene sulfonamide ammonium chloride ruthenium; ammonium formate / dichloromethane / 24 h / 70 °C / 2016.93 Torr / Inert atmosphere

3: copper(l) iodide; caesium carbonate / N,N-dimethyl-formamide / 1 h / 45 °C / Inert atmosphere

4: trifluoroacetic acid / acetonitrile / 3 h / 30 - 35 °C / Inert atmosphere

With copper(l) iodide; N-[(1R,2R)-1,2-diphenyl-2-(3-phenylpropylamino)ethyl]-4-methylbenzene sulfonamide ammonium chloride ruthenium; ammonia; ammonium formate; caesium carbonate; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ol500971c

upstream raw materials:

5-bromo-2-(2-(2,5-dibromophenyl)-1-iminoethyl)phenol

(R)-2-(1-amino-2-(2,5-dibromophenyl)ethyl)-5-bromophenol

(R)-5-bromo-2-(5-bromoindolin-2-yl)phenol

benzaldehyde

Downstream raw materials:

(S)-3,10-dibromo-6-phenyl-6H-benzo[5,6][1,3]oxazino[3,4-a]-indole

(2S,2'S)-di-tert-butyl 2,2'-(5,5'-((S)-6-phenyl-6H-benzo[5,6][1,3]oxazino[3,4-a]indole-3,10-diyl)bis(1H-imidazole-5,2-diyl))bis(pyrrolidine-1-carboxylate) 4-nitrobenzoic acid

6-phenyl-3,10-bis(2-((S)-pyrrolidin-2-yl)-1H-imidazol-5-yl)-6H-benzo[5,6][1,3]oxazino[3,4-a]indole

N,N'-[[(6S)-6-phenyl-6H-indolo[1,2-c][1,3]benzoxazine-3,10-diyl]bis[1H-imidazole-5,2-diyl-(2S)-2,1-pyrrolidinediyl-[(1S)-1-(1-methylethyl)-2-oxo-2,1-ethanediyl]]]bis[carbamic acid] C,C'-dimethyl ester

Refernces

• 1、 -. "PROCESS FOR PREPARING TETRACYCLIC HETEROCYCLE COMPOUNDS". . . Retrieved 2015/05/19.
• 2、 Li, Hongmei,Chen, Cheng-Yi,Nguyen, Hoa,Cohen, Ryan,Maligres, Peter E.,Yasuda, Nobuyoshi,Mangion, Ian,Zavialov, Ilia,Reibarkh, Mikhail,Chung, John Y. L.. "Asymmetric synthesis of cyclic indole aminals via 1,3-stereoinduction". . p. 8533 - 8540. Retrieved 2015/01/08.