Potassium Phosphate, Tribasic → Methyl 2-chloro-6-[methyl(methylsulfonyl)amino]isonicotinate

Participants

Reaction Conditions

Reaction Steps

Methyl 2,6-dichloroisonicotinate (25 g, 121.3 mmol), methyl(methylsulfonyl)amine (3.18 g, 29.12 mmol), potassium phosphate (38.6 g, 182 mmol), Xantphos (4.2 g, 7.28 mmol) and tris(dibenzylideneacetone)dipalladium (2.22 g, 2.43 mmol) were added to a dry, argon flushed flask. Dioxane (1200 mL) was added, the solution degassed with argon and the reaction was heated to 100° C. for 16 hours. The reaction was cooled to rt, filtered through celite and evaporated in vacuo. Flash chromatography (silica, 0-50% 0 to 40% EtOAc in hexane) gave methyl 2-chloro-6-[methyl(methylsulfonyl)amino]isonicotinate as a yellow oil: 1H NMR (400 MHz, CDCl3) δ 7.88 (s, 1H), 7.68 (s, 1H), 3.96 (s, 3H), 3.44 (s, 3H), 3.11 (s, 3H).

Provenance & Evidence