Benzophenone imine → 6-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]-N-(diphenylmethylene)pyridin-3-amine

Participants

Reaction Conditions

Reaction Steps

2-[4-(5-chloropyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole (100 mg, 0.30 mmol), benzophenone imine (60 μL, 0.36 mmol), Pd2(dba)3 (15 mg, 0.015 mmol), 1,1′-biphenyl-2-yl(dicyclohexyl)phosphine (10 mg, 0.015 mmol), NaOtBu (40 mg, 0.42 mmol) were combined in a sealable tube evacuated and backfilled with argon. Toluene (600 μL) was added and the mixture was degassed with a stream of argon for 5 min. The tube was sealed and the mixture was heated to 80° C. for 24 h. Crude mixture was adsorbed onto silica gel and purified by automated flash chromatography using an EtOAc/hexanes gradient to afford 6-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]-N-(diphenylmethylene)pyridin-3-amine as a yellow solid.

Provenance & Evidence