Sodium hydride → HCID 18952386, compound

Participants

Reaction Steps

Sodium hydride (60% dispersion in oil, 51 mg) was added to a solution of compound F (440 mg) in tetrahydrofuran (15 ml) under an atmosphere of argon. The mixture was stirred for 20 minutes and then methyl-α-bromophenylacetate (320 mg) in tetrahydrofuran (5 ml) was added. The mixture was stirred for 18 hours and then volatile material was removed by evaporation. The residue was partitioned between ethyl acetate (25 ml) and water (25 ml) and the organic layer was separated, washed with saturated sodium chloride solution (25 ml) and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by flash chromatography, eluting with methanol/dichloromethane (1:199 v/v) to give methyl 2-[4-((5,7-diethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-1-yl)methyl)-2-propylphenoxy]phenylacetate (A) (300 mg) as an oil; NMR: 0.9(t, 3H), 1.2(t, 3H), 1.35(t, 3H), 1.55-1.7(m, 2H), 2.7(t, 2H), 2.8(q, 2H), 3.1(q, 2H), 5.4(s, 2H), 5.6(s, 1H), 6.65(d, 1H), 6.75(d, 1H), 6.9(s, 1H), 6.95(d, 1H), 7.1(s, 1H), 7.3-7.4(m, 3H), 7.5-7.6(m, 2H), 7.95(d, 1H).

Provenance & Evidence