Methane → N-(5-Fluoropyridin-2-yl)pivalamide

Participants

Reaction Steps

To a solution of 33.6 mL triethylamine and 22.5 2-amino-5-fluoropyridine (0.201 mol) in 200 mL dichloromethane was added dropwise a solution of 28 mL pivaloyl chloride (0.201 mol) in 50 mL dichloromethane at such a rate that the temperature did not exceed 15° C. (ice bath cooling). The mixture was then stirred overnight with thawing to room temperature. To the resulting brown-black suspension was added 5 g charcoal and the mixture was stirred at room temperature for 30 min and filtered through dicalite. The orange- yellow mother liquor was purified by filtration over a layer of silica gel (400 g) with heptane:ethyl acetate=4:1. The slightly yellow product fractions were evaporated and the oily residue was distilled in a kugelrohr apparatus at 100° C. and 0.5 mbar. The compound crystallized on standing at room temperature.

Provenance & Evidence