Triethylamine → 6-[5-(4-Fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylethynyl]-nicotinic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-ethynyl-4-(4-fluoro-phenyl)-1-methyl-1H-[1,2,3]triazole (101 mg, 0.5 mmol), methyl 6-bromonicotinate (130 mg, 0.6 mmol), triethylamine (174 μL, 1.25 mmol) and PdCl2(PPh3)2 (11 mg, 0.3 mol %) in DMF (1 mL) was evaporated and flushed with Ar five times. Then CuI (2 mg, 0.2 mol %) was added and the reaction mixture was stirred at 90° C. for 30 min and DMF (1 mL) was added. The mixture was then poured into sodium hydroxide solution (1 M) and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 0 to 50% ethyl acetate in heptane) afforded the title compound (133 mg, 79%) as a light yellow solid. MS: m/e=337.1 [M]+.

Provenance & Evidence