N-bromobutanimide → methyl 3-bromo-6-(methyloxy)-1H-indole-2-carboxylate

HRID 1874795Notes

Reaction equation

HRID 1874795 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[NH:9]2)=[CH:5][CH:4]=1.[Br:16]N1C(=O)CCC1=O>CN(C=O)C>[Br:16][C:7]1[C:6]2[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[NH:9][C:8]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 688173Methyl-6-methoxy-2-indolecarboxylate

Product 1

HCID 22141396methyl 3-bromo-6-(methyloxy)-1H-indole-2-carboxylateYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 6-(methyloxy)-1H-indole-2-carboxylate (0.10 g, 0.49 mmol) was dissolved in DMF (2 mL) then N-bromosuccinimide (0.095 g, 0.53 mmol) added and the reaction stirred for 38 h. The solvent was evaporated and the reaction mixture was purified by column chromatography (hexanes/EtOAc) to afford the title compound (0.075 g, 54%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.08 (s, 1H), 7.41 (d, 1H), 6.82-6.89 (m, 2H), 3.88 (s, 3H), 3.80 (s, 3H). MS: m/z 284.0 (M+1).

Workup

  1. customThe solvent was evaporated
  2. customthe reaction mixture was purified by column chromatography (hexanes/EtOAc)

Sources & evidence

ORD record
ord-245842d6ddf7459886a8c888d4fb0470
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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