Methyl 2-azido-3-(2-bromophenyl)prop-2-enoate → methyl 4-bromo-1H-indole-2-carboxylate

HRID 1384815Notes

Reaction equation

HRID 1384815 reaction equation
[N:1]([C:4](=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[Br:16])[C:5]([O:7][CH3:8])=[O:6])=[N+]=[N-]>C1(C)C=CC=CC=1>[Br:16][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[NH:1]2

Participants

3

Reactant 1

HCID 78114796Methyl 2-azido-3-(2-bromophenyl)prop-2-enoate

Product 1

HCID 4714973methyl 4-bromo-1H-indole-2-carboxylateYield 11.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 116 g (0.41 mol) of methyl 2-azido-3-(2-bromophenyl)prop-2-enoate in 1.5 l of toluene is added dropwise over 4 h, with mechanical stirring, to a solution of 2 l of toluene heated to reflux and reflux is maintained for an additional 1 h. The solvent is evaporated under reduced pressure and the residue is taken up in 2 l of cyclohexane. The precipitate is collected by filtration, washed with toluene and dried under reduced pressure 37.85 g (149 mmol) of product are isolated. The mother liquors are concentrated under reduced pressure and the residue is purified by chromatography on a column of silica gel. 12.2 g (48 mmol) of additional product are isolated.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. temperaturereflux
  4. temperatureis maintained for an additional 1 h
  5. customThe solvent is evaporated under reduced pressure
  6. filtrationThe precipitate is collected by filtration
  7. washwashed with toluene
  8. customare isolated
  9. concentrationThe mother liquors are concentrated under reduced pressure
  10. customthe residue is purified by chromatography on a column of silica gel

Sources & evidence

ORD record
ord-095b05646f0a4e3cbbece6ddf3e7d5da
Source dataset
uspto-grants-2001_07
Patent number
US06262045B1

Reaction notes

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