Water → HCID 9943313, compound

Participants

Reaction Conditions

Reaction Steps

To a −60° C. solution of 2-(4-chloro-5-fluoro-3-methylpyridin-2-yl)-2-cyclopropylacetamide (2.7 g, 11.0 mmol (Example 1)) and triphosgene (7.2 g, 24.0 mmol) in dichloromethane (250 mL) was added portionwise potassium tert-butoxide (4.5 g, 40.0 mmol). After the addition was complete, the mixture was stirred at −50° C. for 30 minutes. Water was then added at this temperature. The organic layer was separated, washed with brine (3×), dried over sodium sulfate, filtered, and evaporated. The residue was purified by column chromatography (7:3 ethyl acetate/hexanes) to afford the title compound (2 g). 1H NMR (200 MHz, CDCl3) δ 8.95 (bs, 1H), 8.16 (d, 1H), 2.66 (s, 3H), 1.75-1.71 (m, 1H), 1.11-1.01 (m, 2H), 0.46-0.37 (m, 2H). MSCI: m/z=269 (MH+).

Provenance & Evidence