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

HRID 913691노트

반응식

HRID 913691 반응식
[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]=[CH:39][CH:38]=[C:37]([C:41]([F:44])([F:43])[F:42])[CH:36]=2)[O:32][N:31]=1>C(#N)C>[F:21][C:2]([F:1])([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])[N:7]2[CH2:29][C:30]1[N:34]=[C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([F:44])([F:42])[F:43])[CH:36]=2)[O:32][N:31]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 27366223-(Chloromethyl)-5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazoleHCID 578002104-(trifluoromethyl)-2-(3,3,3-trifluoropropyl)-1H-indole-5-carbonitrile

생성물 1

HCID 578005184-(Trifluoromethyl)-1-({5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-2-(3,3,3-trifluoropropyl)-1H-indole-5-carbonitrile수율 24%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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, 2.612 mmol) and 3-(chloromethyl)-5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole (0.257 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 (0.051 g, 24% yield): MS (ES) m/z 532 (M+).

후처리

  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)

출처 및 근거

ORD 기록
ord-d91d304aee114fcdaa5ae5c51146ac3b
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026262B2

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