Potassium Carbonate → HCID 57526945, compound

Participants

Reaction Conditions

Reaction Steps

To a 250-mL RB-flask containing tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate (4.58 g, 14.8 mmol), K2CO3 (6.14 g, 44.4 mmol) and PdCl2dppf (1.48 mmol, 1.21 g) was added a solution of benzyl 5-bromo-2,4-difluorophenylcarbamate (5.05, 14.8 mmol) in DMF (150 mL) at room temperature under argon. The mixture was heated to 80° C. under argon overnight. After cooling to room temperature, the mixture was filtered through Celite and the Celite was washed with EtOAc (3×100 mL). The filtrates were washed with H2O (3×200 mL), brine (100 mL), dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified flash chromatography (EtOAc/hexanes 1:9) to afford tert-butyl 4-(5-{[(benzyloxy)carbonyl]amino}-2,4-difluorophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate (1.60 g, 24.5%): 1H NMR (400 MHz, CDCl3) δ 8.08 (s, 1H), 7.45-7.35 (m, 5H), 6.85-6.70 (m, 1H), 5.95-5.85 (m, 1H), 5.20 (s, 2H), 4.05 (m, 2H), 3.6-3.5 (m, 2H), 2.5-2.4 (m, 2H), 1.50 (s, 9H); ESMS m/e: 443.3 (M−H+).

Provenance & Evidence