Potassium Carbonate → 6,6-difluoro-2-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine

HRID 570127

반응식

HRID 570127 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[CH2:25][C:26]([F:34])([F:33])[CH2:27]OS(C)(=O)=O)(=O)=O>CN(C=O)C.O>[F:33][C:26]1([F:34])[CH2:27][O:13][C:11]2=[CH:12][C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[N:9][N:10]2[CH2:25]1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 2428712,2-Difluoropropane-1,3-diyl dimethanesulfonateHCID 1785156243-(4-fluorophenyl)-1H-pyrazol-5-ol

생성물 1

HCID 894882296,6-difluoro-2-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine수율 56%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

To a solution of 3-(4-fluorophenyl)-1H-pyrazol-5-ol (4 g, 22.47 mmol) in DMF (30 mL) was added K2CO3 (12.4 g, 89.88 mmol) and 2,2-difluoropropane-1,3-diyl dimethanesulfonate (9 g, 33.7 mmol) at room temperature and then stirred for 16 h at 60° C. The progress of the reaction was monitored by TLC. Thereafter, the reaction mixture was diluted with cold water and extracted with diethyl ether. 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 6,6-difluoro-2-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine (3.2 g, 56%) as an off-white solid.

후처리

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

출처 및 근거

ORD 기록
ord-ca030abcf55f4cd2950e44fc900b0eee
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09023844B2

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