2-Benzyloxy-6-bromopyridine → 6-(benzyloxy)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-bromo-6-benzyloxypyridine (1.10 g, 4.15 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.00 g, 4.57 mmol, 1.1 eq.) in tert-butyl alcohol (20 mL) was added sodium tert-butoxide (556 mg, 5.78 mmol, 1.40 eq.), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (98 mg, 0.25 mmol, 0.06 eq.), and bis(dibenzylideneacetone)palladium(0) (96 mg, 0.17 mmol, 0.04 eq.). The reaction mixture was purged with nitrogen for a few minutes, and the dark orange reaction mixture was heated under microwave irradiation (300 watts, 120° C.) for 15 minutes. The reaction was quenched with 10% aqueous citric acid and poured into ethyl acetate. The organic layer was washed with water and brine, then dried (Na2SO4), filtered and evaporated in vacuo. The resultant residue was purified by column chromotagraphy (Si-PPC, gradient 0 to 100% ethyl acetate in heptane) to give the desired product (l-1) (1.08 g, 65% yield) as slightly brown solid. 1H NMR (CDCl3, 400 MHz) δ ppm 7.75 (d, J=8.4 Hz, 2H), 7.49 to 7.41 (m, 3H), 7.41 to 7.34 (m, 4H), 7.34 to 7.27 (m, 1H), 6.46 (s, 1H), 6.44 (d, J=7.9 Hz, 1H), 6.30 (d, J=7.9 Hz, 1H), 5.37 (s, 2H), 1.34 (s, 12H).

Provenance & Evidence