N-bromobutanimide → tert-Butyl 7-(bromomethyl)-1H-indole-1-carboxylate

HRID 561370Notes

Reaction equation

HRID 561370 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[CH3:17])[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:18]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl>[Br:18][CH2:17][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:16]=1[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:9]=[CH:10]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 21874578tert-Butyl 7-methyl-1H-indole-1-carboxylate

Product 1

HCID 21874701tert-Butyl 7-(bromomethyl)-1H-indole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

200 mg (865 μmol) of the compound from Example 5A were introduced into 10 ml of tetrachloromethane, 169 mg (951 μmol) of N-bromosuccinimide were added, and the mixture was heated under reflux while irradiating with a sun lamp for 4 h. The residue after concentration was purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate gradient) to result in 168 mg (63% of theory) of the title compound.

Workup

  1. additionwere added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux
  4. customwhile irradiating with a sun lamp for 4 h
  5. concentrationThe residue after concentration
  6. customwas purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-912f81984e2f4c23baff2ad2439fb508
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

Loading…