Water → 6-(1-tert-butyl-1H-pyrazol-4-yl)-3-methyl-4-(methylsulfonyl)-3H-imidazo[4,5-c]pyridine
Reaction equation
[C:1]([N:5]1[CH:9]=[C:8]([C:10]2[N:15]=[C:14]([S:16][CH3:17])[C:13]3[N:18]([CH3:21])[CH:19]=[N:20][C:12]=3[CH:11]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:30])C=1.[OH2:33].CCOC(C)=O>C(Cl)Cl>[C:1]([N:5]1[CH:9]=[C:8]([C:10]2[N:15]=[C:14]([S:16]([CH3:17])(=[O:30])=[O:33])[C:13]3[N:18]([CH3:21])[CH:19]=[N:20][C:12]=3[CH:11]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 6-(1-tert-butyl-1H-pyrazol-4-yl)-3-methyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine 2.39 and 6-(1-tert-butyl-1H-pyrazol-4-yl)-3-methyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine 2.40 (1.44 g, 4.78 mmol) in DCM at 0° C. was added mCPBA (2.47 g, 14.3 mmol) and the reaction was stirred for 5 min at 0° C. and warmed to rt for 2 hours. Water (20 mL) and EtOAc (40 mL) were added and the layers were separated and the aqueous was extracted with EtOAc (3×40 mL). The combined organics were washed with saturated NaHCO3 (2×50 mL), dried (MgSO4), filtered and concentrated. The residue was purified by flash chomatrography to afford 6-(1-tert-butyl-1H-pyrazol-4-yl)-3-methyl-4-(methylsulfonyl)-3H-imidazo[4,5-c]pyridine 2.41.
Workup
- temperaturewarmed to rt for 2 hours
- customthe layers were separated
- extractionthe aqueous was extracted with EtOAc (3×40 mL)
- washThe combined organics were washed with saturated NaHCO3 (2×50 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash chomatrography
Sources & evidence
- ORD record
- ord-5d0ef1595097406896d274cc07adbf1d
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376441B2
Reaction notes
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