4-Fluorobenzonitrile → 2-[2-(4-Cyano-phenoxy)-1-hydroxy-1-methyl-ethyl]-6-trifluoromethyl-1H-indole-5-carbonitrile

HRID 1945171

반응식

HRID 1945171 반응식
[OH:1][C:2]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]#[N:16])=[C:10]([C:17]([F:20])([F:19])[F:18])[CH:9]=2)([CH3:5])[CH2:3][OH:4].[H-].[Na+].F[C:24]1[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=1>CN(C=O)C>[C:28]([C:27]1[CH:30]=[CH:31][C:24]([O:4][CH2:3][C:2]([C:6]2[NH:7][C:8]3[C:13]([CH:14]=2)=[CH:12][C:11]([C:15]#[N:16])=[C:10]([C:17]([F:20])([F:18])[F:19])[CH:9]=3)([OH:1])[CH3:5])=[CH:25][CH:26]=1)#[N:29]

참가 물질

5

반응물 3

HCID 145174-FluorobenzonitrileHCID 24758Sodium hydrideHCID 668644952-(1,2-Dihydroxy-1-methyl-ethyl)-6-trifluoromethyl-1H-indole-5-carbonitrile

생성물 1

HCID 668653412-[2-(4-Cyano-phenoxy)-1-hydroxy-1-methyl-ethyl]-6-trifluoromethyl-1H-indole-5-carbonitrile

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-(1,2-dihydroxy-1-methyl-ethyl)-6-trifluoromethyl-1-H-indole-5-carbonitrile (209.6 mg, 0.7374 mmol) in dry DMF (4 ml) was added NaH (60 mg, 1.4749 mmol, 60% in mineral oil). After the reaction mixture was stirred at room temperature for 30 min., 4-fluorobenzonitrile (98.15 mg, 0.8115 mmol) was added, and the reaction mixture stirred at room temperature. After HPLC indicated the consumption of starting material, the reaction mixture was poured onto water and extracted with ethyl acetate. The organic layer was washed with 10% LiCl, brine and dried over MgSO4. Column chromatography (EtOAc/Hexanes 50%-100%) yielded the title product as a light yellow powder.

후처리

  1. stirringthe reaction mixture stirred at room temperature
  2. customthe consumption of starting material
  3. additionthe reaction mixture was poured onto water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with 10% LiCl, brine
  6. dry with materialdried over MgSO4

출처 및 근거

ORD 기록
ord-c04c114f45fc40a993a58966a6d7a589
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394971B2

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