Sodium Methoxide → N-cyclopropyl-5-fluoro4'-[5-(methoxymethyl)-1,3,4-oxadiazol-2-yl]-6-methyl-1,1'-biphenyl-3-carboxamide

Participants

Reaction Steps

Freshly prepared sodium methoxide in methanol (0.2M, 0.8 ml) was added to a solution of (4′-[5-chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-5-fluoro-6-methyl-1,1′-biphenyl-3-carboxamide (Intermediate 34) (50 mg) in methanol (1 ml) and the reaction stirred at room temperature for 18 hours. Further sodium methoxide in methanol (0.2M, 1.6 ml) was added and the reaction continued for 72 hours. The reaction was reduced to dryness under vacuum and the residue partitioned between ethyl acetate and water. The organic phase was reduced to dryness and loaded onto a bond-elut (silica, 10 g). Eluted with an ethyl acetate/cyclohexane gradient. The solvent was evaporated from the product fractions under vacuum to give N-cyclopropyl-5-fluoro4′-[5-(methoxymethyl)-1,3,4-oxadiazol-2-yl]-6-methyl-1,1′-biphenyl-3-carboxamide.

Provenance & Evidence