1-Hexanol → N-{[6-(hexyloxy)pyridin-2-yl]methoxy}-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

Participants

Reaction Conditions

Reaction Steps

To a solution of N-[(6-bromopyridin-2-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.2 g, 0536 mmol, 1 eq.) in 3 ml of toluene were added hexanol (0.071 g, 0.697 mmol, 1.3 eq.), Cs2CO3 (0.227 g, 0.697 mmol, 1.3 eq.), Pd(OAc)2 (0.002 g, 0.011 mmol, 0.02 eq.) and 2-(Di-t-butylphosphino)-1,1′-binapthyl (0.005 g, 0.013 mmol, 0.025 eq.). The vessel was purged with argon and sealed. The reaction was heated in microwave at 150° C. for 600 s (abs-normal fixed-hold) and diluted with 50 ml of EtOAc, filtered through a “celite” pad. The filtrate was evaporated and the residue was purified by chromatography on silica gel to give N-{[6-(hexyloxy)pyridin-2-yl]methoxy}-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.04 g, 17% yield) as a viscous pale brown oil.

Provenance & Evidence