4-bromo-5-(4-chlorophenyl)-1-methyl-1H-imidazole → 5-(4-chlorophenyl)-1-methyl-1H-imidazole-4-carbonitrile

HRID 1506658Notes

Reaction equation

Br[C:2]1[N:3]=[CH:4][N:5]([CH3:14])[C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.[C:15]([Cu])#[N:16]>CN(C=O)C.N1C=CC=CC=1>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]2[N:5]([CH3:14])[CH:4]=[N:3][C:2]=2[C:15]#[N:16])=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 200 °C

Procedure

To 4-bromo-5-(4-chlorophenyl)-1-methyl-1H-imidazole (1.3 g, 4.79 mmol) in DMF (8.4 mL) and pyridine (1.6 mL) was added CuCN (1.3 g, 14.4 mmol). The reaction was heated in a microwave reactor at 200° C. for 35 min. After cooling to ambient temperature, the reaction was quenched by addition of a 3:1 solution of NH4OH/saturated aqueous NH4Cl (60 mL). The reaction was extracted with EtOAc, organics separated, washed with saturated aqueous NaHCO3, and dried with saturated aqueous NaCl. Solvents were removed in vacuo and the residue purified by column chromatography on silica to provide desired product and recovered starting material. The recovered starting material was resubjected to the reaction conditions and purified as above to provide additional desired product. MS (m/z) 218.3 [M+H]+.

Workup

temperatureAfter cooling to ambient temperature
customthe reaction was quenched by addition of a 3:1 solution of NH4OH/saturated aqueous NH4Cl (60 mL)
extractionThe reaction was extracted with EtOAc, organics separated
washwashed with saturated aqueous NaHCO3
dry with materialdried with saturated aqueous NaCl
customSolvents were removed in vacuo
customthe residue purified by column chromatography on silica

Sources & evidence

ORD record: ord-1ff4ca0a83234268a4cba530ae0b5eb6
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09220710B2

Reaction notes

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