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

HRID 1015969ノート

反応式

HRID 1015969 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-162b2bc945a0480491a8f55a45f6a173
出典データセット
uspto-grants-2011_07
特許番号
US07985730B2

反応ノート

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