Triethylamine → HCID 19077544, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-4'-hydroxybiphenyl (747 mg), 3-ethynyl-3-hydroxyquinuclidine (453 mg), bis(triphenylphosphine)-palladium (II) chloride (105 mg), copper (I) iodide (55 mg) and dry triethylamine (5.0 ml) in dry dimethylformamide (10 ml) was stirred at 70° C. under an atmosphere of argon for 4 hours. The reaction mixture was cooled and the dimethylformamide and triethylamine were removed by evaporation. The residue was purified by flash column chromatography on alumina (ICN - Alumina N32-63) using a gradient of 10% methanol in ethyl acetate to 20% methanol in ethyl acetate as eluent to give 3-[(4'-hydroxybiphenyl-4-yl)ethynyl]quinuclidin-3-ol (220 mg) as a solid, m.p. 230-233° C.; microanalysis, found C, 76.7; H, 6.6, N, 4.4%; C21H21NO2 0.5H2O requires C, 76.8; H, 6.7; N, 4.26%; NMR (DMSO-d6): 1.2-1.42(1H, m), 1.5-1.72(1H, m), 1.8-2.0(3H, m), 2.65-2.8(4H, t), 2.8-3.2(2H, d of d), 5.6-5.7(1H, br), 6.8-6.9(2H, d) and 7.48-7.63(6H, m); m/z 320 (M+H).

Provenance & Evidence