1-Chloro-2-nitrobenzene → HCID 23587460, compound

Participants

Reaction Steps

1-Chloro-2-nitrobenzene (3.00 mmol, 475 mg), Pd2(DBA)3 (0.060 mmol, 55 mg), S-Phos (0.18 mmol, 75 mg), 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (4.0 mmol, 1.2 g) and K3PO4 (4.5 mmol, 1.0 g) were loaded into a Schlenk tube containing a stir bar. The tube was capped with a rubber septum, evacuated and refilled with nitrogen. Toluene (5 mL) was added through the septum via a syringe and the tube was sealed with a Teflon screw cap under a flow of nitrogen, and put into an oil bath at 100° C. The reaction was allowed to stir at this temperature for about 15 hours, then the reaction mixture was cooled to room temperature and filtered through celite. The filtrate was concentrated in vacuo and the resulting residue was purified using flash column chromatography on silica gel (eluent: 14% EtOAc in Hexane) to provide 4-(2-nitro-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester as a brown solid 660 mg, 72%). 1H NMR (400 MHz, CDCl3) δ 7.90 (dd, J=8.0, 1.6 Hz, 1H), 7.58-7.53 (m, 1H), 7.44-7.39 (m, 1H), 7.30-7.27 (m, 1H), 5.62-5.58 (m, 1H), 4.04-4.01 (m, 2H), 3.64 (t, J=5.2 Hz, 2H), 2.36-2.30 (m, 2H), 1.49 (s, 9H).

Provenance & Evidence