tert-Butanol → HCID 68739684, compound

HRID 2261266Notes

Reaction equation

HRID 2261266 reaction equation
C([N:4]1[C:9](=[O:10])[C:8]([Br:11])=[CH:7][C:6]2[CH:12]=[N:13][N:14]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=3[F:22])[C:5]1=2)C=C.C[N+]1([O-])CC[O:27]CC1.[C:31]([OH:35])(C)([CH3:33])[CH3:32]>O.S([O-])([O-])=O.[Na+].[Na+]>[Br:11][C:8]1[C:9](=[O:10])[N:4]([CH2:32][CH:31]([OH:35])[CH2:33][OH:27])[C:5]2[N:14]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=3[F:22])[N:13]=[CH:12][C:6]=2[CH:7]=1

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 68739064HCID 68739064, compound

Product 1

HCID 68739684HCID 68739684, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 24437Sodium SulfiteSolvent

Procedure

A solution of 7-allyl-5-bromo-1-(2,4-difluorophenyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (265 mg, 0.724 mmol) in tert-BuOH (5 mL) and water (5 mL) at RT was treated with 4-methylmorpholine N-oxide (127 mg, 1.09 mmol) and potassium osmate dihydrate (10 mg, 0.027 mmol). The resulting mixture was allowed to stir for 16 h at RT, then diluted with an aqueous solution of sodium sulfite (10 mL) and extracted with EtOAc (3×25 mL). The organic extracts were dried over MgSO4, filtered and concentrated. The crude residue was purified on the ISCO 12 g column (0-5% MeOH:DCM) affording the title compound as a white amorphous solid. MS (ESI, pos.ion) m/z: 399.0/401.0 (M+1).

Workup

  1. extractionextracted with EtOAc (3×25 mL)
  2. dry with materialThe organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified on the ISCO 12 g column (0-5% MeOH:DCM)

Sources & evidence

ORD record
ord-05ea2388d69a43aa97d2f515b3bef084
Source dataset
uspto-grants-2010_12
Patent number
US07846944B2

Reaction notes

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