Phosphorus oxychloride → HCID 57708073, 화합물

HRID 659708노트

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HRID 659708 반응식
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]3[N:13]([CH3:19])[C:14](=[O:18])[CH:15]=[C:16](O)[C:11]=3[CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1.P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:16]1[C:11]2[CH:10]=[N:9][N:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)[C:12]=2[N:13]([CH3:19])[C:14](=[O:18])[CH:15]=1

참가 물질

3

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HCID 24813Phosphorus oxychlorideHCID 577080711-(3-Fluorophenyl)-4-hydroxy-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one

생성물 1

HCID 57708073HCID 57708073, 화합물

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온도
90 °C

실험 절차

A mixture of 1-(3-fluorophenyl)-4-hydroxy-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (2.15 g, 8.27 mmol) and phosphorous oxychloride (10.0 mL, 107 mmol) was heated at 90° C. in an oil bath for 2.5 h. The excess POCl3 was removed on the rotovap and the resulting orange residue was treated with ice and solid Na2CO3 with stirring, and extracted 3×100 mL with EtOAc. The combined EtOAc layers were washed with brine, dried over MgSO4 and concentrated. Purification of the resulting crude material on an ISCO (40 g column, eluting with a gradient of 25-60% EtOAc in Hexanes) provided the title compound as a yellow crystalline solid. MS (ESI, pos.ion) m/z: 278.1 (M+1).

후처리

  1. customThe excess POCl3 was removed on the rotovap
  2. additionthe resulting orange residue was treated with ice and solid Na2CO3
  3. extractionextracted 3×100 mL with EtOAc
  4. washThe combined EtOAc layers were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customPurification of the resulting crude material on an ISCO (40 g column
  8. washeluting with a gradient of 25-60% EtOAc in Hexanes)

출처 및 근거

ORD 기록
ord-5ef79b56717c421090cb2a8429dc51f3
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08080546B2

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