Toluene → HCID 10163553, compound

Participants

Reaction Steps

A flask was charged with 2-(2-chlorophenyl)-1-(4-chlorophenyl)-N-(4-piperidinyl)-1H-imidazole-4-carboxamide (Example 37) (100 mg, 0.24 mmol), 2-bromopyridine (0.55 mg, 0.22 mmol), Pd2(dba)3 (38 mg, 0.24 mmol), BINAP (1.18 mg, 0.0019 mmol), NaOtBu (33.6 mg, 0.35 mmol), and toluene (2 mL). The reaction mixture was heated at reflux overnight, cooled to rt, and diluted with CH2Cl2. The solid was filtered off. The solvent was evaporated. The residue was purified by flash chromatography (33% EtOAc in hexane) to give the product 2-(2-chlorophenyl)-1-(4-chlorophenyl)-N-[1-(2-pyridinyl)-4-piperidinyl]-1H-imidazole-4-carboxamide (55 mg, 47% yield): LC-MS m/z 492.1 (MH+), retention time 2.47 min (method 1); Rf=0.33 (50% EtOAc in hexane).

Provenance & Evidence