Dimethylformamide → HCID 66836014, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-[(3-bromophenyl)(1-methylpiperidin-4-yloxy)methyl]benzothiazole (200 mg) in N,N-dimethylformamide (2.5 mL) and water (0.2 mL) are added copper(I) cyanide (180 mg), bis(dibenzylidenacetone)palladium (14.3 mg) and Xantphos (14.4 mg). The tube is evacuated, filled with argon and sealed. After stirring at 120° C. for 48 h, the mixture is diluted with water then extracted with ethyl acetate. The pooled organic extracts are washed with water, brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 100/0/0 to 92.5/7.5/0.75) to afford 3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)methyl]benzonitrile

Provenance & Evidence