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

Base Information

• Chemical Name: (S)-3,10-dibromo-6-phenyl-6H-benzo[5,6][1,3]oxazino[3,4-a]indole
• CAS No.: 1392102-38-3
• Molecular Formula: C21H13Br2NO
• Molecular Weight: 455.148
• Mol file: 1392102-38-3.mol

Synonyms:(S)-3,10-dibromo-6-phenyl-6H-benzo[5,6][1,3]oxazino[3,4-a]indole;(6S)-3,10-Dibromo-6-phenyl-6H-indolo[1,2-c][1,3]benzoxazine;6H-Indolo[1,2-c][1,3]benzoxazine, 3,10-dibromo-6-phenyl-, (6S)-

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

Chemical Property:

• Appearance/Colour: white
• Boiling Point: 606.8±55.0 °C(Predicted)
• PSA: 14.16000
• Density: 1.68±0.1 g/cm3(Predicted)
• LogP: 6.77260

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 20 articles about (S)-3,10-dibromo-6-phenyl-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: 98.0%

(6S,12aR)-3,10-dibromo-6-phenyl-12,12a-dihydro-6H-benzo-[5,6][1,3]oxazino[3,4-a]indole (1585969-16-9) → (S)-3,10-dibromo-6-phenyl-6H-benzo[5,6][1,3]oxazino[3,4-a]-indole (1392102-38-3)

Guidance literature:

With C₃₁H₂₇BI₂N₂; In N,N-dimethyl-formamide; at 20 ℃; for 20h; Irradiation;

Reference yield: 81.0%

tert.-butylhydroperoxide (75-91-2) + (6S,12aR)-3,10-dibromo-6-phenyl-12,12a-dihydro-6H-benzo-[5,6][1,3]oxazino[3,4-a]indole (1585969-16-9) → (S)-3,10-dibromo-6-phenyl-6H-benzo[5,6][1,3]oxazino[3,4-a]-indole (1392102-38-3) + (6S,12aR)-3,10-dibromo-12a-(tert-butylperoxy)-6-phenyl-6H-benzo[5,6][1,3]oxazino[3,4-a]indol-12(12aH)-one

Guidance literature:

With copper diacetate; potassium carbonate; In acetonitrile; at 20 ℃; for 72h; Inert atmosphere;

DOI:10.1021/acs.joc.6b01854

Reference yield:

4'-bromo-2'-hydroxyacetophenone (30186-18-6) → (S)-3,10-dibromo-6-phenyl-6H-benzo[5,6][1,3]oxazino[3,4-a]-indole (1392102-38-3) + (R)-3,10-dibromo-6-phenyl-6H-benzo[5,6][1,3]oxazino[3,4-a]-indole (1392102-37-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetic acid / ethanol / Reflux

1.2: PPA / 110 °C

2.1: potassium carbonate / N,N-dimethyl-formamide / 100 °C

With potassium carbonate; acetic acid; In ethanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2016.06.063

upstream raw materials:

4'-bromo-2'-hydroxyacetophenone

C₁₄H₁₂Br₂N₂O

5-bromo-2-(5-bromo-1H-indol-2-yl)phenol

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

Downstream raw materials:

(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