Cesium carbonate → [1-(3,5-Difluoro-benzyl)-3-(2-nitro-phenylsulfanyl)-1H-indol-6-ylamino]-acetonitrile

HRID 1158839ノート

反応式

HRID 1158839 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].[F:7][C:8]1[CH:9]=[C:10]([CH:32]=[C:33]([F:35])[CH:34]=1)[CH2:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([NH2:21])[CH:19]=2)[C:14]([S:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[N+:29]([O-:31])=[O:30])=[CH:13]1.Br[CH2:37][C:38]#[N:39]>CN(C)C=O>[F:7][C:8]1[CH:9]=[C:10]([CH:32]=[C:33]([F:35])[CH:34]=1)[CH2:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([NH:21][CH2:37][C:38]#[N:39])[CH:19]=2)[C:14]([S:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[N+:29]([O-:31])=[O:30])=[CH:13]1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 594638551-(3,5-Difluoro-benzyl)-3-(2-nitro-phenylsulfanyl)-1H-indol-6-ylamine

生成物 1

HCID 11518048[1-(3,5-Difluoro-benzyl)-3-(2-nitro-phenylsulfanyl)-1H-indol-6-ylamino]-acetonitrile収率 12%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

Cesium carbonate (3.8 g, 11.7 mmol) was added to an ice-cooled solution of 1-(3,5-difluoro-benzyl)-3-(2-nitro-phenylsulfanyl)-1H-indol-6-ylamine (Example 15a; 3.2 g, 7.79 mmol) in dry dimethyl formamide (15 ml). After 15 min. stirring, bromoacetonitrile (7.4 g, 62.3 mmol) was added and the reaction mixture was heated at 80° C. for 2 h. The mixture was quenched with water and the product was extracted into ethyl acetate. The combined organic phases were washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography (toluene/acetone 95:5) and crystallization from acetonitrile afforded the title compound (0.42 g). 1H-NMR (CDCl3) δ 8.27 (dd, 1H, J=8.4 and 1.6 Hz), 7.37 (d, 1H, J=8.6 Hz), 7.32 (s, 1H), 7.31 (ddd, 1H, J=8.4, 7.4 and 1.6 Hz), 7.19 (ddd, 1H, J=8.4, 7.4 and 1.6 Hz), 6.99 (dd, 1H, J=8.4 and 1.6 Hz), 6.76 (tt, 1H, J=8.6 and 2.0 Hz), 6.67 (m, 2H), 6.64 (dd, 1H, J=8.6 and 2.0 Hz), 6.54 (d, 1H, J=2.0 Hz), 5.32 (s, 2H), 4.13 (d, 2H, J=6.6 Hz), 4.04 (t, 1H, J=6.6 Hz).

後処理

  1. customThe mixture was quenched with water
  2. extractionthe product was extracted into ethyl acetate
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customColumn chromatography (toluene/acetone 95:5) and crystallization from acetonitrile

出典と根拠

ORDレコード
ord-d8ce3226560e49fcae28dbeddd95337f
出典データセット
uspto-grants-2010_10
特許番号
US07812036B2

反応ノート

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