Potassium Carbonate → tert-butyl 4-(2-(3-methoxy-3-oxopropyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

To Methyl 3-(2-bromophenyl)propanoate (715 mg, 2.94 mmol) and 3,6-dihydro-2H-pyridine-1-N-Boc-4-boronic acid pinacol ester (1.0 g, 3.23 mmol) were added to a flask, followed by Pd(dppf)Cl2 (151 mg, 0.21 mmol) and K2CO3 (1.22 g, 8.82 mmol). The reaction flask was purged with Ar (3×). Dry DMF (22 mL) was added and the solution was degassed for 10 min. The reaction mixture was heated to 85° C. overnight. The mixture was filtered through Celite and was concentrated. The crude residue was purified by silica gel chromatography (gradient, 10% to 30% EtOAc/hexanes) to give tert-butyl 4-(2-(3-methoxy-3-oxopropyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (23) as a pale yellow oil (970 mg, 96% yield). 1H NMR (400 MHz, CDCl3): δ 7.21-7.16 (m, 3H), 7.09-7.06 (m, 1H), 5.57-5.55 (m, 1H), 4.03 (q, 2H), 3.67 (s, 3H), 3.63 (t, 2H), 2.95-2.91 (m, 2H), 2.59-2.55 (m, 2H), 2.37-2.33 (m, 2H), 1.50 (s, 9H). LC/MS RT (5 min method)=2.10 min. Mass observed: 246.19 (M-Boc+H).

Provenance & Evidence