Water → methyl 6-bromo-1-isopropyl-1H-indole-3-carboxylate

HRID 2078659Notes

Reaction equation

HRID 2078659 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:14]([OH:16])=[O:15])=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[C:17](=O)([O-])[O-].[K+].[K+].IC.O>CN(C)C=O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:14]([O:16][CH3:17])=[O:15])=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 224972346-bromo-1-isopropyl-1H-indole-3-carboxylic acid

Product 1

HCID 57443353methyl 6-bromo-1-isopropyl-1H-indole-3-carboxylateYield 93.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromo-1-isopropyl-1H-indole-3-carboxylic acid (1.94 g) in N,N-dimethylformamide (97 ml) were added potassium carbonate (1.43 g) and iodomethane (0.514 ml) at room temperature under nitrogen, and the mixture was stirred at the same temperature for 3.5 hours. The resulting mixture was poured into water and the aqueous layer was extracted with ethyl acetate. The organic layer was washed successively with water three times and brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=10/1 to 5/1) to give methyl 6-bromo-1-isopropyl-1H-indole-3-carboxylate (1.9 g).

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washThe organic layer was washed successively with water three times and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=10/1 to 5/1)

Sources & evidence

ORD record
ord-111f4f4c7de84fd0bc24e84698822f3c
Source dataset
uspto-grants-2011_04
Patent number
US07928264B2

Reaction notes

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