Azide → 2,2-Difluoro-2-pyridin-2-ylethaneamine

Participants

Reaction Steps

A stirred solution of 100 mg of 2-(2-azido-1,1-difluoro-ethyl)-pyridine was hydrogenated in 10 mL of ethyl acetate over 100 mg of 10% palladium on carbon using a balloon for 1 h. The catalyst was removed by filtration and the solvents removed at reduced pressure. A total of 1.8 g (9.7 mmol) of the azide was reduced using this procedure to give 2,2-difluoro-2-pyridin-2-yl-ethylamine as a yellow oil: 1H NMR (CDCl3) δ 8.66 (d, 1H, 4.2 Hz), 7.82 (td,1H, 7.7, 1.7 Hz), 7.68 (d, 1H, 8.1 Hz), 7.37–7.40 (m, 1H), 3.44 (t, 2H, 14.3 Hz), 1.41 (br s, 2H).

Provenance & Evidence