4-Toluenesulfonyl chloride → N-[4-({3-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3,5-difluorophenyl]acetamide

HRID 2192150ノート

反応式

HRID 2192150 の反応式
[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[O:11][C:12]2[C:17]([F:18])=[CH:16][C:15]([NH:19][C:20](=[O:22])[CH3:21])=[CH:14][C:13]=2[F:23])[NH:4][CH:3]=1.C([Li])CCC.[C:29]1([CH3:39])[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>C1COCC1>[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[O:11][C:12]2[C:17]([F:18])=[CH:16][C:15]([NH:19][C:20](=[O:22])[CH3:21])=[CH:14][C:13]=2[F:23])[N:4]([S:35]([C:32]2[CH:33]=[CH:34][C:29]([CH3:39])=[CH:30][CH:31]=2)(=[O:37])=[O:36])[CH:3]=1

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 59740988N-{4-[(3-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3,5-difluorophenyl}acetamideHCID 178418339Butyllithium

生成物 1

HCID 59741006N-[4-({3-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3,5-difluorophenyl]acetamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

1.37 g (3.58 mmol) of N-{4-[(3-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3,5-difluorophenyl}acetamide are dissolved in 200 ml of THF and cooled to −78° C. 1.6 ml (4.0 mmol) of a 2.5M n-butyllithium solution are added dropwise, and the mixture is stirred for 15 min. 752 mg (3.94 mmol) of p-toluenesulfonyl chloride as a solution in 7.5 ml of THF are then added dropwise. The reaction solution is allowed to warm to RT and stirred for one hour. The mixture is then partitioned between ethyl acetate and 0.1N aqueous sodium hydroxide solution. The aqueous phase is extracted twice with ethyl acetate. The combined organic phases are dried over magnesium sulfate and the solvent is removed under reduced pressure. The product is purified by column chromatography on silica gel (mobile phase: dichloromethane/acetone 20:1 to 10:1).

後処理

  1. temperatureto warm to RT
  2. stirringstirred for one hour
  3. customThe mixture is then partitioned between ethyl acetate and 0.1N aqueous sodium hydroxide solution
  4. extractionThe aqueous phase is extracted twice with ethyl acetate
  5. dry with materialThe combined organic phases are dried over magnesium sulfate
  6. customthe solvent is removed under reduced pressure
  7. customThe product is purified by column chromatography on silica gel (mobile phase: dichloromethane/acetone 20:1 to 10:1)

出典と根拠

ORDレコード
ord-caf2a0b0e8364f32a6ca99ba40c66cfe
出典データセット
uspto-grants-2012_12
特許番号
US08329716B2

反応ノート

読み込み中…