Dimethylformamide → Methyl N-methylindole-6-carboxylate

HRID 576633노트

반응식

HRID 576633 반응식
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]

참가 물질

5

반응물 4

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

생성물 1

HCID 639843Methyl N-methylindole-6-carboxylate

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-0a2a662cff4e429cbe8f337f1575ba15
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040504B2

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