Dimethylformamide → Methyl N-methylindole-6-carboxylate

HRID 2208596Notes

Reaction equation

HRID 2208596 reaction equation
IC.N1C2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([OH:14])=[O:13])[CH:10]=2)[CH:5]=C1.[C:15](=O)([O-])[O-].[K+].[K+].[CH3:21][N:22]([CH:24]=O)[CH3:23]>>[CH3:15][O:14][C:12]([C:9]1[CH:10]=[C:23]2[C:6]([CH:5]=[CH:24][N:22]2[CH3:21])=[CH:7][CH:8]=1)=[O:13]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5952301H-indole-6-carboxylic acid

Product 1

HCID 639843Methyl N-methylindole-6-carboxylate

Procedure

Iodomethane (2.3 mL, 36.9 mmol) was added to a suspension of indole-6-carboxylic acid (1.55 g, 9.62 mmol) and potassium carbonate (1.98 g, 14.3 mmol) in DMF (32 mL) under argon. The reaction was stirred at room temperature for 24 hr. The reaction was quenched with sat. NH4Cl and extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude product was purified by flash chromatography on silica gel (0-60% EtOAc:Hexane). ESI-MS m/z 190 (MH)+.

Workup

  1. customThe reaction was quenched with sat. NH4Cl
  2. extractionextracted with ethyl acetate (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography on silica gel (0-60% EtOAc:Hexane)

Sources & evidence

ORD record
ord-c2c822c5945840dbb299061ba100129d
Source dataset
uspto-grants-2016_06
Patent number
US09376454B2

Reaction notes

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