Hydrochloric Acid → 5-Bromo-6-(2,2,2-trifluoroethoxy)-pyridin-3-ylamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-bromo-5-nitro-2-(2, 2, 2-trifluoro-ethoxy)-pyridine (2.4 g, 7.97 mmol) in ethanol (100 ml) were added HCl (0.3 ml) and stannous chloride (10.5 g, 55.81 mmol) at 25° C. and the reaction mixture was stirred for 4 h at 25° C. After total consumption of starting material (monitored by TLC), ethanol was evaporated under reduced pressure, diluted with ethyl acetate, neutralized with aqueous Na2CO3 solution, and filtered through a bed of celite. The organic layer was separated and the aqueous layer was further extracted with ethyl acetate (2×120 ml). The combined organic layer was washed with brine, dried over Na2SO4 and evaporated in vacuo to get the desired compound (2.1 g, 97%) as brown liquid. This was used as such for the next step without further purification. MS (LC/MS): not responding, NMR is in agreement with the structure: 1H-NMR (400 MHz, CDCl3): δ 4.70 (m, 2H), 7.30 (d, 1H), 7.54 (d, 1H).

Provenance & Evidence