Ammonia → 7-Chloro-1-(cyclohexylmethyl)-1H-indole-3-carboxamide

HRID 2358458ノート

反応式

HRID 2358458 の反応式
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:16]=1[N:15]([CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[CH:14]=[C:13]2[C:24]([OH:26])=O.[NH3:27].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[Cl:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:16]=1[N:15]([CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[CH:14]=[C:13]2[C:24]([NH2:27])=[O:26]

参加物

6

反応物 4

HCID 222AmmoniaHCID 11430Potassium CarbonateHCID 65578Oxalyl chlorideHCID 686740091-cyclohexylmethyl-7-chloro-1H-indole-3-carboxylic acid

生成物 1

HCID 686750957-Chloro-1-(cyclohexylmethyl)-1H-indole-3-carboxamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Oxalyl chloride (4.95 g, 39.0 mmol) was added dropwise to a mixture of 7-chloro-1-(cyclohexyl)methyl-1H-indole-3-carboxylic acid (6.4 g, 21.9 mmol) and dichloromethane (150 ml) under ice-water cooling and the resulting mixture was stirred at room temperate for 20 h. Dichloromethane and excess oxalyl chloride were removed by evaporation and the obtained residue was mixed with dichloromethane (100 ml). Aqueous ammonia (33%, 50 ml) and potassium carbonate (6.05 g, 43.8 mmol) was added into the mixture under ice-water bath cooling. After stirring at room temperature for 2 h, the reaction mixture was concentrated in vacuo, then the obtained solid was washed with water, then n-heptane, and dried under reduced pressure to afford 7-chloro-1-(cyclohexyl)methyl-1H-indole-3-carboxylic acid amide (6.4 g, 22.0 mmol).

後処理

  1. customDichloromethane and excess oxalyl chloride were removed by evaporation
  2. additionthe obtained residue was mixed with dichloromethane (100 ml)
  3. temperaturecooling
  4. stirringAfter stirring at room temperature for 2 h
  5. concentrationthe reaction mixture was concentrated in vacuo
  6. washthe obtained solid was washed with water
  7. dry with materialn-heptane, and dried under reduced pressure

出典と根拠

ORDレコード
ord-d3d88f9275d34e9f83923c752baed0ed
出典データセット
uspto-grants-2010_07
特許番号
US07763732B2

反応ノート

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