Trifluoroacetic acid → (S)-1-(3-Phenyl-3H-imidazo[4,5-b]pyridin-2-yl)propylamine

Participants

Reaction Steps

To a solution of [(S)-1-(3-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)propyl]carbamic acid tert-butyl ester (1.27 g, 3.60 mmol) in DCM (25 mL) was added TFA (10 mL) and the mixture stirred at RT for 15 min. The volatiles were removed in vacuo and the resulting residue dissolved in DCM and washed with a saturated solution of NaHCO3. The aqueous phase was extracted with DCM (×3) and the combined organic fractions dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-8% 2M NH3/MeOH in DCM) to afford the title compound as a brown oil (440 mg, 40% over 3 steps). 1H NMR (CDCl3, 400 MHz): δ 8.34 (1H, d, J=4.82 Hz), 8.08 (1H, d, J=8.00 Hz), 7.67-7.52 (3H, m), 7.45 (2H, d, J=7.60 Hz), 7.30-7.22 (1H, m), 3.99 (1H, t, J=6.70 Hz), 2.02-1.87 (1H, m), 1.83-1.69 (3H, m), 0.89 (3H, t, J=7.40 Hz).

Provenance & Evidence