2-(2-bromophenyl)-3-methyl-2H-azirine → 4-Bromo-2-methyl-1H-indole

HRID 475113Notes

Reaction equation

HRID 475113 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:10]([CH3:11])=[N:9]1>C1(C)C(C)=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH:8]=[C:10]([CH3:11])[NH:9]2

Participants

3

Reactant 1

HCID 712717232-(2-bromophenyl)-3-methyl-2H-azirine

Product 1

HCID 218145664-Bromo-2-methyl-1H-indoleYield 75.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

The solution of 2-(2-bromophenyl)-3-methyl-2H-azirine (758 mg, 3.61 mmol) in xylene (20 mL) was stirred at 160° C. for 7 d. The reaction mixture was concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (10:1) to afford 4-bromo-2-methyl-1H-indole as yellow oil (572 mg, 75.5%). MS (ESI): m/z=210.1 [M+1]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by SiO2 chromatography
  3. washeluting with petroleum ether/EtOAc (10:1)

Sources & evidence

ORD record
ord-a2cea392b0b44911ae2ad43a2a5142e0
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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