Sodium Chloride → 4-[(3-bromo-2-(2-(2-triphenylmethyl-2H-tetrazol-5-yl)phenyl)benzofuran-5-yl)methoxy]-2-ethyl-5,6,7,8-tetrahydroquinoline

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A mixture of 5,7-diethyl-1,6-naphthyridin-2(1H)-one (291 mg), 5-[2-(3-bromo-5-(bromomethyl)benzofuran-2-yl)phenyl]-2-triphenylmethyl-2H-tetrazole (1.30 g), potassium t-butoxide (168 mg) and 1,4,7,10,13,16-hexaoxacyclooctadecane (40 mg) in dry tetrahydrofuran (15 ml) was stirred under an atmosphere of argon for 18 hours. Saturated sodium chloride solution (25 ml) was added and the mixture was extracted with ether (2×25 ml). The extracts were dried (MgSO4) and concentrated by evaporation. The residue was purified by flash chromatography, eluting with ethyl acetate/hexane (3:1 v/v), to give 1-[(3-bromo-2-(2-(2-triphenylmethyl-2H-tetrazol-5-yl)phenyl)benzofuran-5-yl)methyl]-5,7-diethyl-1,6-naphthyridin-2(1H)-one (A) (640 mg) as a foam; NMR: 1.2(t, 3H), 1.35(t, 3H), 2.7(q, 2H), 3.1(q, 2H), 5.6(s, 2H), 6.8-7.25(m, 19 H), 7.35(s, 1H), 7.5-7.7(m, 3H), 8.0(d, 1H), 8.2(d, 1H).

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