2,4-Difluoronitrobenzene → HCID 178496652, compound

Participants

Reaction Steps

To a solution of 2,4-difluoro-1-nitrobenzene (0.2 mL, 1.7 mmol) in CH3CN (3 mL) were added trans-3-methoxycyclobutylamine (0.18 g, 1.7 mmol) and DIPEA (0.3 mL, 1.7 mmol). The reaction mixture was stirred at RT for 18 h then concentrated in vacuo. The resulting residue was carried to the next step without further purification (0.41 g, quantitative). To a solution of the product thus obtained (1.7 mmol) in EtOAc (15 mL) was added Pd/C (350 mg) and the reaction mixture was stirred at RT for 18 h under a hydrogen atmosphere. The suspension was filtered through a pad of Celite® and the filtrate was concentrated in vacuo to afford the title compound as a dark oil (0.36 g, quantitative). 1H NMR (CDCl3, 300 MHz): δ 6.68-6.59 (1H, m), 6.33 (1H, dt, J=19.6 Hz, 2.7 Hz), 6.18 (1H, dd, J=13.6 Hz, 2.7 Hz), 4.00-3.90 (1H, m), 3.76-3.63 (1H, m), 3.53 (3H, br s), 3.27 (3H, s), 2.49-2.37 (2H, m), 2.36-2.12 (2H, m).

Provenance & Evidence