Triethylamine → HCID 19434138, compound

Participants

Reaction Steps

In 2 mL of dichloromethane, the product of Step C (0.07 g) was combined with tetrakis(triphenylphosphine)palladium(0) (0.010 g), copper(I) iodide (0.006 g), triphenylphosphine (0.006 g), (4-fluorophenyl)acetylene (prepared by the method of A.D. Allen and C. D. Cook, Can. J. Chem. (1963), 41, 1084; 0.15 g), and triethylamine (2 mL) and the mixture heated at reflux until thin layer chromatographic analysis showed consumption of starting material. The mixture was concentrated in vacuo. The residue was purified by chromatography on silica gel to afford the title product, a compound of this invention, as a solid melting at 95°-110° C. (material prepared on larger scale, identical by 1H NMR spectroscopy, was recrystallized from ethyl acetate/hexane to give a solid melting at 102°-104° C.). 1H NMR (CDCl3) δ2.0 (m, 1H), 2.4 (m, 1H), 4.3 (m, 1H), 4.5 (m, 1H), 4.8 (m, 1H), 6.9-7.1 (m,4H), 7.3-7.4 (m,3H), 7.5-7.6 (m,4H).

Provenance & Evidence