Potassium Carbonate → N-[4-({3-Cyclopropyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3-fluorophenyl]acetamide

HRID 2192165ノート

反応式

HRID 2192165 の反応式
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[CH:14][C:13]=2[F:22])[N:4]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:39]1(B(O)O)[CH2:41][CH2:40]1>CN(C=O)C.ClCCl.CO>[CH:39]1([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[CH:8][C:9]=3[O:11][C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[CH:14][C:13]=3[F:22])[N:4]([S:23]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH:3]=2)[CH2:41][CH2:40]1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 2760897Cyclopropylboronic acidHCID 59740993N-[4-({3-bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3-fluorophenyl]acetamide

生成物 1

HCID 59740992N-[4-({3-Cyclopropyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3-fluorophenyl]acetamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 21226129Dichloromethane methanol溶媒

反応条件

温度
110 °C

実験手順

500 mg (0.96 mmol) of N-[4-({3-bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3-fluorophenyl]acetamide and 400 mg (2.89 mmol) of potassium carbonate are suspended in DMF (5 ml). The solution is degassed and vented with argon. 39 mg (0.05 mmol) of [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride/methylene dichloride complex and 207 mg (2.41 mmol) of cyclopropylboronic acid (Wallace, Debra J.; Chen, Cheng-yl; Tetrahedron Lett. 2002, 43(39), 6987-6990) are then added. The mixture is heated at 110° C. overnight. The reaction mixture is then dissolved in dichloromethane/methanol 10:1 and filtered through an Extrelut cartridge. The filtrate is concentrated under reduced pressure and the crude product is purified by preparative HPLC.

後処理

  1. customThe solution is degassed
  2. filtrationfiltered through an Extrelut cartridge
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. customthe crude product is purified by preparative HPLC

出典と根拠

ORDレコード
ord-71cbb23083894701abca66a511dd8759
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…