Dimethylformamide → 4-Methyl-2-((2S,3R)-3-methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidine-1-carbonyl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of (2-bromo-5-methylphenyl)((2S,3R)-3-methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidin-1-yl)methanone (synthesized from Example A3, 0.35 g, 0.744 mmol), Zn(CN)2 (0.105 g, 0.818 mmol), Pd2(dba)3 (0.068 g, 0.074 mmol) and 2-dicyclohexylphophino-2′,6′-dimethoxybiphenyl (S-Phos; 0.076 g, 0.186 mmol) in wet DMF (DMF:H2O 10:1, 20 mL) was degassed and sealed and heated in a microwave reactor for 1 h at 150° C. The reaction was cooled to rt and the solvent was removed in vacuo. The crude was dissolved with EtOAc, washed with satd. aq. NaHCO3 and brine and dried over Na2SO4. The solvent was removed and the crude was purified in silica gel with 0˜100% EtOAc/Hex to obtain the title compound. ESI-MS (m/z): 417 [M+1]+.

Provenance & Evidence