Isopropanol → 4-(6-Fluoro-1-methyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenol

HRID 573360ノート

反応式

HRID 573360 の反応式
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[C:22](F)=[CH:21][C:20]([F:24])=[CH:19][N:18]=2)=O)=[CH:11][CH:10]=1)C1C=CC=CC=1.[CH3:25][NH:26][NH2:27].CC(O)C>O>[F:24][C:20]1[CH:21]=[C:22]2[N:26]([CH3:25])[N:27]=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=3)[C:17]2=[N:18][CH:19]=1

参加物

5

反応物 3

HCID 3776IsopropanolHCID 6061MethylhydrazineHCID 66727888[4-(Benzyloxy)phenyl](3,5-difluoropyridin-2-yl)methanone

生成物 1

HCID 1364090944-(6-Fluoro-1-methyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenol収率 55.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of [4-(benzyloxy)phenyl](3,5-difluoropyridin-2-yl)methanone (300 mg), methylhydrazine (212 mg) and 2-propanol (5 mL) was stirred at room temperature for 30 min, and then at 90° C. for 12 h, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The crude material was dissolved in EtOH (20 mL) and 10% Pd—C (50% wet, 98 mg) was added. The mixture was stirred for 1 h under H2 atmosphere, filtered and evaporated. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (125 mg).

後処理

  1. waitat 90° C. for 12 h
  2. extractionextracted with AcOEt
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe crude material was dissolved in EtOH (20 mL)
  6. addition10% Pd—C (50% wet, 98 mg) was added
  7. stirringThe mixture was stirred for 1 h under H2 atmosphere
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

出典と根拠

ORDレコード
ord-ab891d5c13054a37af200483cb4a3a3a
出典データセット
uspto-grants-2015_05
特許番号
US09029536B2

反応ノート

読み込み中…