General procedure for the synthesis of (6-amino-5-bromopyridin-3-yl)methanol from ethyl 6-amino-5-bromonicotinate:
A) Ethyl 6-amino-5-bromonicotinate (2.31 g, 10 mmol) was dissolved in tetrahydrofuran (20 mL) at room temperature and lithium aluminum hydride (LAH, 10 mL, 1 M solution in tetrahydrofuran) was added slowly and dropwise. The reaction mixture was stirred for 1 h. The reaction was quenched by careful addition of water (0.2 mL). The resulting precipitate was collected by filtration and washed with ethyl acetate. The filtrate was concentrated under reduced pressure to give (6-amino-5-bromopyridin-3-yl)methanol (2.0 g, 99% yield) as a white solid. The product was confirmed by LC/MS analysis showing (M + H)+ = 203, 205 (ratio 1:1).1H NMR (CD3OD, 300 MHz) data were as follows: δ 7.79 (s, 1H), 7.67 (s, 1H), 4.35 (br s, 2H).
