Sodium hydride → 5-[5-(4-Fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-pyrazine-2-carboxylic acid methyl ester

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Reaction Steps

To a suspension of NaH (55% in oil, 131 mg, 3.0 mmol) in THF (3.9 mL) was added a solution of [5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-yl]-methanol (622 mg, 3.0 mmol) in THF (7.9 mL) dropwise at 0° C. and the reaction mixture was stirred at room temperature for 30 min. Then a solution of methyl 5-chloropyrazine-2-carboxylate (569 mg, 3.3 mmol) in THF (7.9 mL) was added dropwise at 0° C. and the reaction mixture was stirred at room temperature for 16 h. The mixture was then poured into ice water 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, then 0 to 5% methanol in dichloromethane) afforded the title compound (474 mg, 46%) as an off white gum. MS: m/e=344.1 [M+H]+.

Provenance & Evidence