Potassium Carbonate → 6-(4-Fluorophenyl)-2,3-dimethyl-2,3-dihydropyrazolo[5,1-b][1,3]oxazole

HRID 570129

반응식

HRID 570129 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([OH:13])[NH:10][N:9]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].CS(O[CH:25]([CH:27](OS(C)(=O)=O)[CH3:28])[CH3:26])(=O)=O>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[C:11]3[O:13][CH:25]([CH3:26])[CH:27]([CH3:28])[N:10]3[N:9]=2)=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 999092,3-Butanediol, dimethanesulfonateHCID 1785156243-(4-fluorophenyl)-1H-pyrazol-5-ol

생성물 1

HCID 894883126-(4-Fluorophenyl)-2,3-dimethyl-2,3-dihydropyrazolo[5,1-b][1,3]oxazole수율 71.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a solution of 3-(4-fluorophenyl)-1H-pyrazol-5-ol (3 g, 16.8 mmol) in DMF (15 mL) was added K2CO3 (9.3 g, 67.4 mmol) and butane-2,3-diyl dimethanesulfonate (4.8 g, 18.5 mmol) (prepared as described in US2010/41748) at room temperature and then stirred for 16 h at 60° C. Thereafter, the reaction mixture was diluted with cold water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and concentrated to get the crude product. Purification by column chromatography over silica gel (eluent 5-10% ethyl acetate in petrol ether) yielded 6-(4-fluorophenyl)-2,3-dimethyl-2,3-dihydropyrazolo[5,1-b][1,3]oxazole (2.8 g, 71%) as yellow oil and a mixture of diastereoisomers.

후처리

  1. customprepared
  2. customat room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. customto get the crude product
  7. customPurification by column chromatography over silica gel (eluent 5-10% ethyl acetate in petrol ether)

출처 및 근거

ORD 기록
ord-5fdc646e557142ff9c0d88ee8192ca33
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09023844B2

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