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

Participants

Reaction Conditions

Reaction Steps

Methyl 2,6-dichloroisonicotinate (10 g, 48.5 mmol), methyl(propylsulfonyl)amine (7.99 g, 58.2 mmol), potassium phosphate (14.4 g, 68 mmol), Xantphos (1.69 g, 2.9 mmol) and tris(dibenzylideneacetone)dipalladium (0.89 g, 0.97 mmol) were added to a dry, argon flushed flask. Dioxane (400 mL) was added, the solution degassed with argon and the reaction was heated to 100° C. for 16 h. The reaction was cooled to rt, filtered through celite and evaporated in vacuo. Flash chromatography (silica, 0-35% EtOAc/hexanes) gave methyl 2-chloro-6-[(methylsulfonyl)(propyl)amino]isonicotinate as a yellow oil: 1H NMR (400 MHz, CD3OD) δ 7.88 (s, 1H), 7.72 (s, 1H), 3.96 (s, 3H), 3.91 (t, J=6.4 Hz, 2H), 3.13 (s, 3H), 1.68-1.53 (m, 2H), 0.93 (t, J=7.5 Hz, 3H).

Provenance & Evidence