Dimethylformamide → 6-Chloro-1,2-dimethyl-1H-indole-3-carboxylic acid methyl ester

HRID 2261843노트

반응식

HRID 2261843 반응식
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[CH3:15])=[O:4].[C:16](=O)([O-])[O-].[K+].[K+].IC.CN(C=O)C>C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[N:7]([CH3:16])[C:6]=1[CH3:15])=[O:4]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57443356methyl 6-chloro-2-methyl-1H-indole-3-carboxylate

생성물 1

HCID 574433576-Chloro-1,2-dimethyl-1H-indole-3-carboxylic acid methyl ester수율 55.8%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 6-chloro-2-methyl-1H-indole-3-carboxylic acid methyl ester (2.76 g, 12.3 mmol), potassium carbonate (6.80 g, 49.2 mmol), iodomethane (1.07 mL, 17.2 mmol) and DMF (36 mL) is stirred overnight at room temperature. The mixture is diluted with ethyl acetate, washed twice with water, washed with brine and dried (MgSO4) and concentrated. The residue is triturated in 25 mL of 1:3 ethyl acetate-heptane and filtered to provide 1.63 g (55%) of pure title product. Additional material can be obtained through further trituration of the mother liquor. ES/MS m/e 238.0 (M+1).

후처리

  1. washwashed twice with water
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue is triturated in 25 mL of 1:3 ethyl acetate-heptane
  6. filtrationfiltered

출처 및 근거

ORD 기록
ord-a725026dd39e47ea924ac6d0a3c206d1
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07846960B2

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