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

HRID 573360노트

반응식

HRID 573360 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ab891d5c13054a37af200483cb4a3a3a
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029536B2

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