Hydrochloric Acid → (3-bromopyridin-2-yl)methanaminehydrochloride

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution of 3-bromo-2-cyanopyridine (975.0 mg, 5.328 mmol) in THF (30 mL) was added borane (1.0 M in THF, 27.0 mL, 27.0 mmol) slowly via addition funnel over the course of 15 min. The reaction was stirred at 0° C. for 45 min and then warmed to RT for 17 h. After cooling to 0° C., the reaction was quenched with methanol (35 mL) and concentrated. The residue was dissolved in dichloromethane (6 mL) and charged with hydrochloric acid (4.0 M in 1,4-dioxane, 5 mL, 20 mmol) and then concentrated to afford 1.574 g (>100%) of the title compound as a yellow solid. The crude material thus obtained was used without further purification. MS (ESI): 187.09, 189.12 [M+H]+; HPLC tR=0.67 & 0.97 min (ZQ3: polar—5 min).

Provenance & Evidence