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

HRID 570127

反応式

HRID 570127 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ca030abcf55f4cd2950e44fc900b0eee
出典データセット
uspto-grants-2015_05
特許番号
US09023844B2

関連ノート

読み込み中…