Phosphorus oxychloride → HCID 57708073, compound

HRID 659708Notes

Reaction equation

HRID 659708 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

HCID 57708073HCID 57708073, compound

Conditions

Temperature
90 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-5ef79b56717c421090cb2a8429dc51f3
Source dataset
uspto-grants-2011_12
Patent number
US08080546B2

Reaction notes

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