Water → 3-Amino-6-(4-(2-hydroxyethoxy)-3-(trifluoromethyl)phenyl)-4-(methylamino)-picolinonitrile

Participants

Reaction Steps

2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)phenoxy)ethanol (7.1 g), 3-amino-6-chloro-4-(methylamino)picolinonitrile (21.38 mmol, 3.90 g), potassium phosphate, tribasic (13.61 g), tricyclohexylphosohine (0.719 g), and tris(dibenzylideneacetone)dipalladium(0) (0.979 g) were dissolved in Dioxane (100 ml) and Water (40.0 ml) and stirred under nitrogen at 100° C. for 3 hrs. The mixture was diluted with ethyl acetate and filtered through celite. Filtrate was washed with water (300 ml), organic layer extracted and concentrated in vacuo to give crude 3-amino-6-(4-(2-hydroxyethoxy)-3-(trifluoromethyl)phenyl)-4-(methylamino)picolinonitrile (11 g). 1H NMR (MeOH) δ: 8.07 (s, 1H), 8.00 (d, 1H), 7.70 (m, 1H), 7.42 (m, 1H), 7.25 (m, 1H), 4.20 (t, 2.5), 3.93 (t, 2.5), 3.66 (s, 1.5), 2.98 (s, 3.5). MS m/z 353 (M+H).

Provenance & Evidence