Sodium Bicarbonate → 2-cyano-2-{4-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-2-yl}-N,N-dimethyl-acetamide

HRID 886574ノート

反応式

HRID 886574 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([C:24](=O)[C:25]([N:27]([CH3:29])[CH3:28])=[O:26])[CH:19]=3)[CH:16]=2)[N:11]([S:31]([C:34]2[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=2)(=[O:33])=[O:32])[CH:10]=1.COC1C=CC=CC=1C1C2C(=NC=C(B3OC(C)(C)C(C)(C)O3)C=2)[N:51](S(C2C=CC(C)=CC=2)(=O)=O)[CH:50]=1.BrC1C=CN=C(C(C#N)C(N(C)C)=O)C=1.C(=O)(O)[O-].[Na+]>C(#N)C.C1(C)C=CC=CC=1>[C:50]([CH:24]([C:20]1[CH:19]=[C:18]([C:15]2[CH:16]=[C:17]3[C:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[O:2][CH3:1])=[CH:10][N:11]([S:31]([C:34]4[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=4)(=[O:32])=[O:33])[C:12]3=[N:13][CH:14]=2)[CH:23]=[CH:22][N:21]=1)[C:25]([N:27]([CH3:28])[CH3:29])=[O:26])#[N:51]

参加物

7

反応物 4

HCID 516892Sodium BicarbonateHCID 160390673-(2-Methoxyphenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 598250242-{4-[3-(2-Methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-2-yl}-N,N-dimethyl-2-oxo-acetamideHCID 598250762-(4-bromo-pyridin-2-yl)-2-cyano-N,N-dimethyl-acetamide

生成物 1

HCID 598250262-cyano-2-{4-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-2-yl}-N,N-dimethyl-acetamide

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

2-{4-[3-(2-Methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-2-yl}-N,N-dimethyl-2-oxo-acetamide was 3-(2-methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (493 mg, 0.977 mmol), 2-(4-bromo-pyridin-2-yl)-2-cyano-N,N-dimethyl-acetamide (80%, 391 mg, 1.46 mmol) and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II)-dichloride dichloromethane adduct (39.8 mg, 0.048 mmol) were combined in a vial under nitrogen and dissolved in acetonitrile (2.5 mL) and toluene (2.5 mL). Saturated sodium bicarbonate (5 mL) was added and the system was purged with nitrogen gas. The reaction mixture was capped and heated for 15 h at 80° C. The cooled mixture was diluted with ethyl acetate and washed with brine. The combined organic layers were dried over sodium sulfate and purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes to afford 2-cyano-2-{4-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-2-yl}-N,N-dimethyl-acetamide.

後処理

  1. customthe system was purged with nitrogen gas
  2. customThe reaction mixture was capped
  3. additionThe cooled mixture was diluted with ethyl acetate
  4. washwashed with brine
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. custompurified by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-8d175634073c43f396f09c0df8687de0
出典データセット
uspto-grants-2012_08
特許番号
US08242280B2

反応ノート

読み込み中…