Dimethylformamide → 3-[2-(4-[2-Methyl-tetrazol-5-yl]phenyl)ethynyl]-3-hydroxyquinuclidine

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-ethynyl-3-hydroxyquinuclidine (0.3 g), 2-methyl-5-(4-bromophenyl)tetrazole (0.48 g), bis(triphenylphosphine)-palladium (II) chloride (70 mg), copper (I) iodide (35 mg), triethylamine (1 ml) and dimethylformamide (2 ml) was stirred at 70° C. for 2 hours. The mixture was diluted with dichloromethane (4 ml) and filtered down a short column of silica (Varian Bond-sluts S1 silica) eluting with a gradient of 0:100 (v/v) to 100:0 (v/v) methanol/dichloromethane. The appropriate organic fractions were combined, washed with saturated aqueous sodium carbonate (3×30 ml), dried (Na2CO3) and evaporated to give 3-[2-(4-[2-methyl-tetrazol-5-yl]phenyl)ethynyl]-3-hydroxyquinuclidine (260 mg) as a solid, m.p. 228°-230° C.; microanalysis, found: C, 65.9; H, 6.1; N, 22.2%; C17H19N5O requires: C, 66.0; H, 6.2; N, 22.6%; NMR: 1.2-1.4(1H,m), 1.5-1.7(1H,m), 1.8-2.0(3H,m), 2.7(4H,m), 2.8-3.2(2H,m), 4.4(3H,s), 5.6(1H,s), 7.6(2H,m), 8.05(2H,m); m/z 310(M+H).

Provenance & Evidence