2,4-Difluoronitrobenzene → HCID 178496651, compound

Participants

Reaction Steps

To a solution of 2,4-difluoro-1-nitrobenzene (0.18 mL, 1.6 mmol) in CH3CN (3 mL) were added cis-3-methoxycyclobutylamine (0.17 g, 1.6 mmol) and DIPEA (0.28 mL, 1.6 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 any further purification (0.39 g, quantitative). To a solution of the product thus obtained (1.6 mmol) in EtOAc (15 mL) was added Pd/C (350 mg) and the reaction mixture stirred at RT for 18 h under a hydrogen atmosphere. The suspension was filtered through a pad of Celite® and the filtrate concentrated in vacuo to afford the title compound as a dark oil (0.453 g, quantitative). 1H NMR (CDCl3, 300 MHz): δ 6.67-6.06 (1H, m), 6.35-6.17 (2H, m), 3.75-3.63 (1H, m), 3.61-3.25 (3H, br s), 3.22 (3H, s), 3.12-2.93 (1H, m), 2.90-2.78 (2H, m), 1.85-1.60 (2H, m).

Provenance & Evidence