Cesium carbonate → HCID 57800503, 화합물

HRID 2102092노트

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HRID 2102092 반응식
[CH2:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[C:10]([C:13]([F:16])([F:15])[F:14])[C:9]([C:17]#[N:18])=[CH:8][CH:7]=2)[CH2:2][CH3:3].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:26][C:27]1[N:31]=[C:30]([C:32]2[S:33][CH:34]=[CH:35][CH:36]=2)[O:29][N:28]=1>C(#N)C>[CH2:1]([C:4]1[N:5]([CH2:26][C:27]2[N:31]=[C:30]([C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)[O:29][N:28]=2)[C:6]2[C:11]([CH:12]=1)=[C:10]([C:13]([F:15])([F:16])[F:14])[C:9]([C:17]#[N:18])=[CH:8][CH:7]=2)[CH2:2][CH3:3]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 594028453-(Bromomethyl)-5-(2-thienyl)-1,2,4-oxadiazoleHCID 674051552-propyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

생성물 1

HCID 57800503HCID 57800503, 화합물수율 64.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 2-propyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile (Example 153A) (0.150 g, 0.595 mmol) in anhydrous acetonitrile (25 mL) was added Cs2CO3 (0.193 g, 0.595 mmol) and 3-(bromomethyl)-5-(2-thienyl)-1,2,4-oxadiazole (0.213 g, 0.893 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 (0.159 g, 64% yield): MS (ES) m/z 416 (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-4881b6a7a94c46a0bd13b3ddc132811f
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572820B2

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