反应详情

温度

85 °C

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).

1. customThe reaction flask was purged with Ar (3×)
2. additionDry DMF (22 mL) was added
3. customthe solution was degassed for 10 min
4. filtrationThe mixture was filtered through Celite
5. concentrationwas concentrated
6. customThe crude residue was purified by silica gel chromatography (gradient, 10% to 30% EtOAc/hexanes)