Carbon tetrabromide → 6-(4-(3-bromopropyl)-3-(trifluoromethyl)-phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile

Participants

Reaction Conditions

Reaction Steps

6-[4-(3-Hydroxypropyl)-3-(trifluoromethyl)-phenyl]-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile (1.3 g) was gently heated in THF (36 ml) until all dissolved and then cooled to 0° C. in an ice bath. Carbon tetrabromide (2.4 g) was added followed by triphenylphosphine (1.9 g). The mixture was stirred at 0° C. for 15 minutes and then at room temperature for 20 minutes until the cloudy suspension became a clear solution. The reaction mixture was diluted with DCM (100 ml) and washed with water (100 ml×2). Organic layer was dried over sodium sulphate and solvent was evaporated under reduced pressure. The residue was then columned (100 g SiO2 column, 1:1 EtOAc/Heptane to EtOAc gradient) to afford 6-(4-(3-bromopropyl)-3-(trifluoromethyl)-phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile (1.2 g) as a white solid.

Provenance & Evidence