2,4-Difluoronitrobenzene → HCID 178496651, compound

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).

1. concentrationthen concentrated in vacuo
2. customThe resulting residue was carried to the next step without any further purification (0.39 g, quantitative)
3. customTo a solution of the product thus obtained (1.6 mmol) in EtOAc (15 mL)
4. stirringthe reaction mixture stirred at RT for 18 h under a hydrogen atmosphere
5. filtrationThe suspension was filtered through a pad of Celite®
6. concentrationthe filtrate concentrated in vacuo

ORD record

ord-20d14064d90f4067858f0add743d7cbd

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653089B2