Iodoethane → HCID 59620027, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-amino-5-bromopyridine (CAS#13535-01-8, 520 mg, 3.0 mmol) in THF (12 mL) at −78° C. was added potassium bis(trimethylsilyl)amide (0.5 M in toluene, 6.9 mL, 3.45 mmol). The reaction was stirred for 20 minutes at −78° C. and was then charged with iodoethane (0.25 mL, 3.15 mmol). The reaction was stiffed for an additional 30 minutes, at which time mixture was charged with additional potassium bis(trimethylsilyl)amide (0.5 M in toluene, 6.9 mL, 3.45 mmol) and iodoethane (0.25 mL, 3.15 mmol). The reaction was then permitted to warm to −20° C. over 2 h at which time it was quenched with aqueous ammonium hydroxide (5 mL) and was stirred for 30 minutes at room temperature. The reaction was then diluted with brine and ethyl acetate. The layers were separated and the aqueous layer was extracted two additional times. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 0 to 60%) to afford both (5-bromo-pyridin-3-yl)-ethyl-amine and (5-bromo-pyridin-3-yl)-diethyl-amine separately.

Provenance & Evidence