Sodium hydride → HCID 19890814, compound

Participants

Reaction Steps

Sodium hydride (60% dispersion in mineral oil; 80 mg) was added to a stirred suspension of the 1,5-naphthyridinone (D1) (320 mg) in N,N-dimethylformamide (DMF) (10 ml). The mixture was stirred until evolution of hydrogen had ceased and then a solution of the bromomethyl compound (C1) in DMF (2 ml) was added. Stirring was continued for 16 hours and then water (100 ml) was added. The mixture was extracted with ethyl acetate (3×25 ml) and the extracts were washed with water (25 ml), followed by saturated sodium chloride solution (25 ml) and dried (MgSO4). The solvent was removed by evaporation and the residue purified by flash chromatography, eluting with methanol/dichloromethane (1:19 v/v) to give methyl 4'-[(2-methyl-1,5-naphthyridin-4-yloxy)methyl]biphenyl-2-carboxylate (A1) (244 mg), as an off-white powder, m.p. 132°-134° C. (from ethyl acetate/hexane); NMR (CDCl3): 2.7(s,3H), 3.6(s,3H), 5.5(s, 2H), 6.9(s,1H), 7.3-7.7 (complex m,3H), 7.85(d,1H), 8.3(dd,1H), 8.9(dd,1H); 13C NMR: (benzylic CH2) 70.6 ppm.

Provenance & Evidence