4-Toluenesulfonyl chloride → N-[4-({3-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}methyl)-3-fluorophenyl]-2,2,2-trifluoroacetamide

HRID 2240248ノート

反応式

HRID 2240248 の反応式
[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])=[CH:14][C:13]=2[F:25])[NH:4][CH:3]=1.C([Li])CCC.[C:31]1([CH3:41])[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1.C(=O)(O)[O-].[Na+]>C1COCC1.O>[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:21])[F:22])=[CH:14][C:13]=2[F:25])[N:4]([S:37]([C:34]2[CH:35]=[CH:36][C:31]([CH3:41])=[CH:32][CH:33]=2)(=[O:39])=[O:38])[CH:3]=1

参加物

7

反応物 4

HCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 59305008N-{4-[(3-Bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)methyl]-3-fluorophenyl}-2,2,2-trifluoroacetamideHCID 178418339Butyllithium

生成物 1

HCID 59304989N-[4-({3-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}methyl)-3-fluorophenyl]-2,2,2-trifluoroacetamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

1.70 g (4.08 mmol) of N-{4-[(3-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)methyl]-3-fluorophenyl}-2,2,2-trifluoroacetamide are dissolved in 50 ml of THF and cooled to −78° C. A solution of n-butyllithium (2.81 ml, 1.6M in hexane, 4.49 mmol) is added dropwise. After 15 min, a solution of 860 mg (4.49 mmol) of p-toluenesulfonyl chloride in 5 ml of THF is added dropwise. The mixture is allowed to warm to RT and stirred for 1 h. Water and saturated sodium bicarbonate solution are then added, and the mixture is extracted with ethyl acetate. The organic phase is dried over sodium sulfate. The solvent is removed under reduced pressure and the residue is purified by column chromatography on silica gel (mobile phase dichloromethane:ethanol=50:1).

後処理

  1. temperatureto warm to RT
  2. extractionthe mixture is extracted with ethyl acetate
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customThe solvent is removed under reduced pressure
  5. customthe residue is purified by column chromatography on silica gel (mobile phase dichloromethane:ethanol=50:1)

出典と根拠

ORDレコード
ord-6644c304aa494962bc83c911a283b8e2
出典データセット
uspto-grants-2010_05
特許番号
US07723347B2

反応ノート

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