Ammonium Chloride → 1-(3-Phenyl-3H-imidazo[4,5-c]pyridin-2-yl)ethanone
Reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:11]1([N:17]2[C:21]3[CH:22]=[N:23][CH:24]=[CH:25][C:20]=3[N:19]=[CH:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CN(C)[C:28](=[O:30])[CH3:29].[Cl-].[NH4+]>C1COCC1>[C:11]1([N:17]2[C:21]3[CH:22]=[N:23][CH:24]=[CH:25][C:20]=3[N:19]=[C:18]2[C:28](=[O:30])[CH3:29])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1Participants
Conditions
- Temperature
- -78 °C
Procedure
LiHMDS (2.0M in THF/heptane/ethyl benzene, 3.9 mL, 7.79 mmol) was added to a stirred solution of 3-phenyl-3H-imidazo[4,5-c]pyridine (0.95 g, 4.87 mol) in THF (20 mL) at −78° C. under nitrogen. The resultant mixture was stirred at −78° C. for 10 minutes then at −10° C. for 15 minutes. The reaction mixture was re-cooled to −78° C. and N,N-dimethylacetamide (0.72 mL, 7.79 mmol) added then stirred at −78° C. for 5 minutes then at −10° C. for 15 minutes. The reaction mixture was poured into saturated aqueous ammonium chloride solution (30 mL) and extracted with EtOAc (3×30 mL). The combined EtOAc extracts were dried (Na2SO4) and concentrated in vacuo. The residue was purified by chromatography (SiO2 0-4% (2M ammonia in methanol) in DCM) to give the title compound as an off white solid (0.96 g, 76%) LCMS (method H): Rt 1.76 min, [M+H]+ 238
Workup
- waitat −10° C. for 15 minutes
- extractionextracted with EtOAc (3×30 mL)
- dry with materialThe combined EtOAc extracts were dried (Na2SO4)
- concentrationconcentrated in vacuo
- customThe residue was purified by chromatography (SiO2 0-4% (2M ammonia in methanol) in DCM)
Sources & evidence
- ORD record
- ord-57d25b3207cd46ccad9cab9fa5600c2f
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653089B2
Reaction notes
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