Water → 2-(5-chloro-1H-indol-1-yl)propanamide

HRID 1991472ノート

反応式

HRID 1991472 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.Br[CH:14]([CH3:18])[C:15]([NH2:17])=[O:16].O>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:14]([CH3:18])[C:15]([NH2:17])=[O:16])[CH:8]=[CH:7]2

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 871105-ChloroindoleHCID 1011182-Bromopropanamide

生成物 1

HCID 591297552-(5-chloro-1H-indol-1-yl)propanamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A dispersion of 60% NaH (6.85 g, 0.17 mol) was added to an ice-cooled solution of 5-chloroindole (20 g, 0.13 mol) in 250 ml of dry DMF. The stirring was continued for 20 minutes at room temperature, and the mixture was cooled again with an ice bath. After portionwise addition of solid 2-bromopropanamide (24.1 g, 0.15 mol), the reaction mixture was stirred for 1 h 30 at room temperature, then poured into cold water and extracted 3 times with AcOEt. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by silica gel chromatography (AcOEt/hexane 50/50) to give pure 2-(5-chloro-1H-indol-1-yl)propanamide 25 as a white solid.

後処理

  1. temperaturethe mixture was cooled again with an ice bath
  2. extractionextracted 3 times with AcOEt
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by silica gel chromatography (AcOEt/hexane 50/50)

出典と根拠

ORDレコード
ord-c5628f0355954a8f828e7352373bc1fd
出典データセット
uspto-grants-2010_01
特許番号
US07645887B2

反応ノート

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