Water → HCID 118207360, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(benzyloxy)-4-bromo-2-fluorobenzene (5.0 g, 17.8 mmol) and tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (6.60 g, 21.3 mmol) in acetonitrile (50 mL) was degassed for 5 min. To this was added water (50 mL), Na2CO3 (5.66 g, 53.4 mmol) and Pd(Ph3P)4 (1.23 g, 1.07 mmol) and the reaction was further degassed for 10 min. It was then heated to 80° C. for 16 h. The reaction cooled to rt, poured into water, and extracted with EtOAc. The combined organic layers were, dried with magnesium sulfate, filtered through celite, and concentrated in vacuo to afford a brown oil. The oil was purified using silica gel column chromatography (0-30% EtOAc/hexanes) to afford 1-butyl 4-(4-(benzyloxy)-3-fluorophenyl)-5,6-dihydropyridine-1(2H)-carboxylate (5.63 g, 83% yield): LC-MS [M+H]+−tBu+ACN=369.2; 1H NMR (500 MHz, DMSO-d6) δ 7.51-7.27 (m, 6H), 7.25-7.13 (m, 2H), 6.12 (br. s., 1H), 5.19 (s, 2H), 3.97 (br. s., 2H), 3.51 (t, J=5.6 Hz, 2H), 2.41 (d, J=1.5 Hz, 2H), 1.42 (s, 9H).

Provenance & Evidence