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

HRID 2261843ノート

反応式

HRID 2261843 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a725026dd39e47ea924ac6d0a3c206d1
出典データセット
uspto-grants-2010_12
特許番号
US07846960B2

反応ノート

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