Potassium Phosphate, Tribasic → 3-Amino-6-(4-(3-hydroxypropoxy)-3-(trifluoromethyl)phenyl)-4-(methylamino)picolinonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoro-methyl)phenoxy)propan-1-ol (34 g), 3-amino-6-chloro-4-(methylamino)picolinonitrile (16.2 g), potassium phosphate (56.5 g), tricyclohexylphosphine (2.98 g), and tris(dibenzylideneacetone)dipalladium(0) (4.06 g) in dioxane (340 ml) and water (170 ml) under N2 was heated to 100° C. for 2 hours then diluted with ethyl acetate and filtered through celite. The organic layer was separated, dried over magnesium sulphate and solvent removed under reduced pressure to give expected product clean enough for use in the next step (49.6 g). 1H NMR (CD3OD) δ: 8.06 (s, 1H), 8.01 (d, 1H), 7.23 (d, 1H), 6.86 (s, 1H), 4.23 (t, 2H), 3.78 (t, 2H), 2.98 (s, 3H), 2.04 (quin, 2H). MS m/z 367 (M+H).

Provenance & Evidence