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

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,6-dibromopyridine (7.1 g, 30.0 mmol), NMP (16 ml), (3-fluorophenyl)methanamine (4.13 g, 33.0 mmol) and Hunig's Base (5.76 ml, 33.0 mmol) was flushed with argon. The crude reaction mixture mixture was stirred at 115-120° C. for about 168 hours. LC/MS was used to monitor the reaction. The crude mixture was then cooled to room temperature, and then diluted with 250 ml of ethyl acetate, washed with saturated sodium bicarbonate (2×), water (2×), saturated, salt solution (1×), dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield a residue. The residue was purified by silica gel chromatography using a 120 g column, eluting from 0%-20% ethyl acetate with hexane. The desired fractions were concentrated to yield, 7.11 grams of the titled compound as a free base, which was used in the next step without further purification. LCMS (m/z): 281.1/283.1 (MH+), retention time=1.03 min.

Provenance & Evidence