Benzonitrile → Pyridine, 4-[2-(4-methoxyphenyl)-1-methyl-4-phenyl-1H-imidazol-5-yl]-

HRID 2293485Notes

Reaction equation

C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][O:14][C:15]1[CH:31]=[CH:30][C:18]([C:19]([N:21]([CH3:29])[CH2:22][C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)=O)=[CH:17][CH:16]=1.[C:32](#[N:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[NH4+].[Cl-]>C1COCC1>[CH3:29][N:21]1[C:22]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)=[C:32]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:39]=[C:19]1[C:18]1[CH:30]=[CH:31][C:15]([O:14][CH3:13])=[CH:16][CH:17]=1

Participants

Conditions

Temperature: -40 °C

Procedure

To a solution of diisopropylamine (0.16 mL, 1.1 mmol) in THF at -78° C. was added n-butyllithium (0.38 mL of 2.5 M solution, 0.95 mmol). To the resulting mixture was added a solution of 4-methoxy-N-methyl-N-(4-picolyl)benzamide (0.16 g, 0.62 mmol) in THF. The resulting dark red solution was warmed to -40° C. and stirred for 15 min, at which time benzonitrile (0.13 mL, 1.2 mmol) was added. The mixture to warmed to rt and stirred for 10 h. Aqueous NH4Cl (0.5 mL,) was added, and the mixture was concentrated under reduced pressure. The residue was purified by flash chromatography, eluting with a solvent gradient of 2-4% MeOH/CHCl3. The material which was isolated was triturated with Et2O and recrystallized from EtOAc to provide the title compound as an off-white solid (35 mg, 17%): nap 193°-194° C.

Workup

additionwas added
temperatureThe mixture to warmed to rt
concentrationthe mixture was concentrated under reduced pressure
customThe residue was purified by flash chromatography
washeluting with a solvent gradient of 2-4% MeOH/CHCl3
customThe material which was isolated
customwas triturated with Et2O
customrecrystallized from EtOAc

Sources & evidence

ORD record: ord-f2eee318c4f04c4a96f25802449b02ba
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05686455

Reaction notes

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