Sodium hydride → 1-(4-{[tert-Butyl(dimethyl)silyl]oxy}cyclohexyl)-3-(trifluoromethyl)-1H-pyrazole

HRID 1025680

반응식

HRID 1025680 반응식
[F:1][C:2]([F:9])([F:8])[C:3]1[CH:7]=[CH:6][NH:5][N:4]=1.[H-].[Na+].CS(O[CH:17]1[CH2:22][CH2:21][CH:20]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:19][CH2:18]1)(=O)=O>CN(C=O)C>[Si:24]([O:23][CH:20]1[CH2:19][CH2:18][CH:17]([N:5]2[CH:6]=[CH:7][C:3]([C:2]([F:9])([F:8])[F:1])=[N:4]2)[CH2:22][CH2:21]1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 18070343-(Trifluoromethyl)pyrazoleHCID 866346564-{[tert-Butyl(dimethyl)silyl]oxy}cyclohexyl methanesulfonate

생성물 1

HCID 595560591-(4-{[tert-Butyl(dimethyl)silyl]oxy}cyclohexyl)-3-(trifluoromethyl)-1H-pyrazole수율 44%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of 3-trifluoromethyl-1H-pyrazole (1.0 g, 7.35 mmol) in DMF (10 mL) cooled in an ice bath was added NaH (0.3 g, 60% in mineral oil). The mixture was stirred for 10 minutes before the mesylate (1.13 g, 3.68 mmol) of step B in DMF (5 mL) was added. Stirring was continued at room temperature for 1 hour and then at 100° C. overnight. After being cooled to room temperature, the solution was poured into ice water and extracted with EtOAc three times. The combined extract was washed with brine, dried over MgSO4 and concentrated. Purification on silica gel eluting with 5:1 EtOAc/hexanes provided the title compound (0.56 g, 44%) as an oil. MS calculated (M+H)+ 349, found 349.

후처리

  1. additionwas added
  2. customat 100° C.
  3. customovernight
  4. extractionextracted with EtOAc three times
  5. extractionThe combined extract
  6. washwas washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customPurification on silica gel eluting with 5:1 EtOAc/hexanes

출처 및 근거

ORD 기록
ord-c9a0eedcd18a491db7fc1d19240bb1b4
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729063B2

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