Acetone → Ethyl 1-(1-methylethyl)-6-[4-(methylsulfonyl)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

HRID 476103Notes

Reaction equation

HRID 476103 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[CH3:7][CH:8]([N:10]1[C:14]2[N:15]=[C:16]([C:24]3[CH:29]=[CH:28][C:27](SC)=[CH:26][CH:25]=3)[CH:17]=[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:13]=2[CH:12]=[N:11]1)[CH3:9].[CH3:32]C(C)=O>O>[CH3:7][CH:8]([N:10]1[C:14]2[N:15]=[C:16]([C:24]3[CH:25]=[CH:26][C:27]([S:3]([CH3:32])(=[O:5])=[O:2])=[CH:28][CH:29]=3)[CH:17]=[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:13]=2[CH:12]=[N:11]1)[CH3:9]

Participants

5

Reactant 3

HCID 180AcetoneHCID 23707502Potassium hydroxy sulfiteHCID 67124392Ethyl 1-(1-methylethyl)-6-[4-(methylthio)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 67124530Ethyl 1-(1-methylethyl)-6-[4-(methylsulfonyl)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Oxone (1712 mg, 2.79 mmol) was added to a solution of ethyl 1-(1-methylethyl)-6-[4-(methylthio)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (330 mg, 0.928 mmol) in acetone (6 mL) and water (2 mL), and the reaction mixture was stirred for 6 h. The reaction mixture was quenched with water (10 mL) and then neutralized with NaHCO3 solution. The mixture was extracted with EtOAc (3×) and the combined extracts dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified using column chromatography (Silica gel, 0 to 100% EtOAc/hexanes) to give 295 mg (82%) of product. LCMS E-S (M+H)=388.1. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.54 (t, J=7.2 Hz, 3H), 1.67-1.69 (d, J=6.8 Hz, 6H), 3.14 (s, 3H), 4.58 (q, J=7.2 Hz, 2H), 5.48 (spt, J=6.7 Hz, 1H), 8.06-8.18 (m, 2H), 8.29 (s, 1H), 8.39-8.44 (m, 2H), 8.47 (s, 1H).

Workup

  1. customThe reaction mixture was quenched with water (10 mL)
  2. extractionThe mixture was extracted with EtOAc (3×)
  3. dry with materialthe combined extracts dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-a14f6e5743ae471e8a760cff533478f4
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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