Dimethylamine → 3-dimethylamino-methyl-1H-indole-6-carboxylic acid methyl ester

HRID 8124

反応式

HRID 8124 の反応式
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[NH:5][CH:4]=1)=[O:2].[CH3:16][NH:17][CH3:18].[BH4-].[Na+].[CH3:21]O>C(Cl)(Cl)Cl.[Cl-].[Na+].O>[NH3:5].[CH3:1][OH:2].[CH3:15][O:14][C:12]([C:8]1[CH:7]=[C:6]2[C:11]([C:3]([N:17]([CH3:18])[CH3:16])=[CH:4][N:5]2[CH3:21])=[CH:10][CH:9]=1)=[O:13]

参加物

8

反応物 4

HCID 674DimethylamineHCID 887MethanolHCID 735867methyl 3-formyl-1H-indole-6-carboxylateHCID 4311764Sodium borohydride

生成物 2

HCID 21705897Ammonia methanol収率 20%HCID 695164543-dimethylamino-methyl-1H-indole-6-carboxylic acid methyl ester収率 99%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
55 °C

実験手順

A solution of methyl 3-formylindole-6-carboxylate (8.0 g, 39.3 mmol) in 270 ml methanol is treated with dimethylamine (40% aqueous; 267 ml, 2.56 mol) at ambient temperature. After 45 minutes, NaBH4 (4.45 g, 118.1 mmol) is added, and the resulting mixture is heated at 55° C. for 3 hours. The reaction mixture is allowed to cool then is diluted with CHCl3 (200 ml) and brine (I 50 ml). The organic layer is washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude residue is purified by flash chromatography (SiO2; 100% ethyl acetate then 20% 2M NH3/methanol in CHCl3) to give 9.07 g of 3-dimethylamino-methyl-1H-indole-6-carboxylic acid methyl ester(99%). Amine 61 is prepared from 3-dimethylaminomethyl-1H-indole-6-carboxylic acid methyl ester by essentially following the procedures detailed in Amine 49, 1 paragraph; and Amine 51, 3rd paragraph.

後処理

  1. temperatureto cool
  2. washThe organic layer is washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude residue is purified by flash chromatography (SiO2

出典と根拠

ORDレコード
ord-3dd918785d8c438daa628a564fa5be31
出典データセット
uspto-grants-2006_08
特許番号
US07087635B2

関連ノート

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