Cesium carbonate → 1-{[5-(3,5-Difluorophenyl)-1,2,4-oxadiazol-3-yl]methyl}-4-(trifluoromethyl)-2-(3,3,3-trifluoropropyl)-1H-indole-5-carbonitrile

HRID 913690ノート

反応式

HRID 913690 の反応式
[F:1][C:2]([F:21])([F:20])[C:3]1[C:11]([C:12]#[N:13])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([CH2:14][CH2:15][C:16]([F:19])([F:18])[F:17])[NH:7]2.C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:29][C:30]1[N:34]=[C:33]([C:35]2[CH:40]=[C:39]([F:41])[CH:38]=[C:37]([F:42])[CH:36]=2)[O:32][N:31]=1>C(#N)C>[F:41][C:39]1[CH:40]=[C:35]([C:33]2[O:32][N:31]=[C:30]([CH2:29][N:7]3[C:8]4[C:4](=[C:3]([C:2]([F:1])([F:20])[F:21])[C:11]([C:12]#[N:13])=[CH:10][CH:9]=4)[CH:5]=[C:6]3[CH2:14][CH2:15][C:16]([F:19])([F:18])[F:17])[N:34]=2)[CH:36]=[C:37]([F:42])[CH:38]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 431202093-(Chloromethyl)-5-(3,5-difluorophenyl)-1,2,4-oxadiazoleHCID 578002104-(trifluoromethyl)-2-(3,3,3-trifluoropropyl)-1H-indole-5-carbonitrile

生成物 1

HCID 578004761-{[5-(3,5-Difluorophenyl)-1,2,4-oxadiazol-3-yl]methyl}-4-(trifluoromethyl)-2-(3,3,3-trifluoropropyl)-1H-indole-5-carbonitrile収率 24%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 4-(trifluoromethyl)-2-(3,3,3-trifluoropropyl)-1H-indole-5-carbonitrile (Example 302A) (0.200 g, 0.653 mmol) in anhydrous acetonitrile (25 mL) was added Cs2CO3 (0.851 g, 0.2.612 mmol) and 3-(chloromethyl)-5-(3,5-difluorophenyl)-1,2,4-oxadiazole (0.226 g, 0.979 mmol). The mixture was heated under N2, for 2 h. Upon cooling, the mixture was partitioned between EtOAc and water. The organic phase was separated, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (0-20% EtOAc-hexanes gradient) to afford a pure product (0.078 g, 24% yield): MS (ES) m/z 500 (M+).

後処理

  1. temperatureThe mixture was heated under N2, for 2 h
  2. temperatureUpon cooling
  3. customthe mixture was partitioned between EtOAc and water
  4. customThe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (0-20% EtOAc-hexanes gradient)

出典と根拠

ORDレコード
ord-706a6bcf7765464799d5c9810e2021a2
出典データセット
uspto-grants-2011_09
特許番号
US08026262B2

反応ノート

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