2-Methoxyethylamine → 2-(4-Bromo-3-[1,3]dioxolan-2-yl-phenoxy)-6-(2-methoxy-ethylamino)-nicotinonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of compound mixture, 6-(4-bromo-3-[1,3]dioxolan-2-yl-phenoxy)-2-chloro-nicotinonitrile and 2-(4-bromo-3-[1,3]dioxolan-2-yl-phenoxy)-6-chloro-nicotinonitrile (4+5, 2.5 g, 6.6 mmol) in acetonitrile (anhydrous, 50 mL) was added 2-methoxy-ethylamine (5.7 mL, 66 mmol). The reaction was heated at 80° C. for 2 hours. After the reaction, all volatile components were evaporated under vacuum. Purification was achieved by silica gel chromatography, eluting with 10%-80% EtOAc/hexanes gradient, affording 1.0 g (36% yield) of the title compound. 1H NMR (400 MHz, chloroform-d) δ ppm 7.58-7.47 (m, 2 H), 7.41 (d, J=3.1 Hz, 1 H), 7.04 (dd, J=8.6, 2.7 Hz, 1 H), 6.09-6.03 (m, 2 H), 5.37 (t, J=5.1 Hz, 1 H), 4.14-3.99 (m, 4 H), 3.37 (t, J=5.1 Hz, 2 H), 3.31-3.23 (m, 5 H).

Provenance & Evidence