Water → HCID 59593376, compound

HRID 910255Notes

Reaction equation

HRID 910255 reaction equation
C(O)(=O)C.[Br:5][C:6]1[C:11](=[O:12])[N:10]([CH3:13])[C:9]2[NH:14][N:15]=[CH:16][C:8]=2[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].I[CH:24]([CH3:26])[CH3:25].O>C1COCC1>[Br:5][C:6]1[C:11](=[O:12])[N:10]([CH3:13])[C:9]2[N:14]([CH:24]([CH3:26])[CH3:25])[N:15]=[CH:16][C:8]=2[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 67198692HCID 67198692, compound

Product 1

HCID 59593376HCID 59593376, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At RT, to a solution of 5-bromo-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one acetic acid adduct (202 mg, 0.701 mmol) in THF (10 mL) was treated with potassium carbonate (290 mg, 2.10 mmol) and 2-iodopropane (0.50 mL, 5.0 mmol). It was heated to reflux for 48 h. The reaction mixture was then treated with water and extracted 2×20 mL EtOAc, dried over MgSO4, filtered and concentrated in vacuo (rotovap). The crude residue was purified on the ISCO (12 g column, 25-90% EtOAc:Hexanes) affording the title compound (88 mg) as a white amorphous solid in >95% purity. MS (ESI, pos.ion) m/z: 270.0/272.0 (M+1).

Workup

  1. temperatureIt was heated
  2. temperatureto reflux for 48 h
  3. extractionextracted 2×20 mL EtOAc
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo (rotovap)
  7. customThe crude residue was purified on the ISCO (12 g column, 25-90% EtOAc:Hexanes)

Sources & evidence

ORD record
ord-dda2ee1f20dd4c239e3878ea3f685908
Source dataset
uspto-grants-2011_09
Patent number
US08022085B2

Reaction notes

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