2,6-Dibromopyridine → 6-bromo-N-(3-fluorobenzyl)pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

To 2,6-dibromopyridine (7.1 g, 30.0 mmol) was added NMP (16 ml), (3-fluorophenyl)methanamine (4.13 g, 33.0 mmol) and Huenig's Base (5.76 ml, 33.0 mmol) flushed with argon. The crude reaction mixture was stirred at 115-120° C. for 168 hr, followed by LCMS. The crude mixture was cooled, 250 ml of ethyl acetate was added, washed with saturated sodium bicarbonate (2×), water (2×), saturated salt solution (1×), dried sodium sulfate, filtered, concentrate. The crude was purified by silica gel chromatography using 120 g column, eluting from 0%-20% ethyl acetate with hexane. The desired fractions were concentrated to constant mass, giving 7.11 grams of the titled compound as a free base used without further purification. LCMS (m/z): 281.1/283.1 (MH+), retention time=1.03 min.

Provenance & Evidence