(5-Fluoro-2-nitrophenyl)pyridin-3-ylamine → 4-Fluoro-N2-pyridin-3-ylbenzene-1,2-diamine

A mixture of (5-fluoro-2-nitrophenyl)pyridin-3-ylamine (1.28 g, 5.49 mmol) in EtOAc (60 mL) was degassed with a stream of nitrogen prior to addition of 10% Pd/C (107 mg) and was stirred at RT under a hydrogen atmosphere for 2 h. The resulting suspension was diluted with IMS (10 mL) and stirred under a hydrogen atmosphere for 56 h. The reaction mixture was filtered through a phase separator and the filtrate concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-20% MeOH in DCM) to afford the title compound as a brown solid (1.03 g, 92%). 1H NMR (CDCl3, 400 MHz): δ 8.24 (1H, d, J=2.67 Hz), 8.14 (1H, d, J=4.50 Hz), 7.20-7.05 (2H, m), 6.86 (1H, dd, J=9.62, 2.63 Hz), 6.79-6.65 (2H, m), 5.42 (1H, s), 3.50 (2H, s)

1. customwas degassed with a stream of nitrogen
2. additionto addition of 10% Pd/C (107 mg)
3. additionThe resulting suspension was diluted with IMS (10 mL)
4. stirringstirred under a hydrogen atmosphere for 56 h
5. filtrationThe reaction mixture was filtered through a phase separator
6. concentrationthe filtrate concentrated in vacuo
7. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-20% MeOH in DCM)

ORD record

ord-2860daa7652c4c2fa0c7206cc6e38da5

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653089B2