Water → HCID 86669144, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-yl)-1,3-oxazinan-2-one (30 mg, 60.9 μmol) in toluene (3 mL) was added a solution of sodium carbonate (64.5 mg, 609 μmol) in EtOH (2 mL)/water (1 mL), 4-iodo-1-methylpyridin-2(1H)-one (14.5 mg, 609 μmol) and Pd(PPh3)4 (7.5 mg, 6 μmol) successively under nitrogen. The mixture was stirred at 100° C. for 2.5 h. The reaction mixture was concentrated under vacuum. The residue was dissolved in water, extracted with EtOAc (5 mL×3). The combined organic layers were dried over Na2SO4, filtered and concentrated under vacuum. The crude product was purified by HPLC to afford 6-(2_hydroxy-2-methylpropyl)-3-(2-(4-(1-methyl-2-oxo-dihydropyridin-4-yl)-6-phenyl-1,3-oxazinan-2-one (10.6 mg, 37%). 1H NMR (CDCl3) δ 7.40-7.19 (m, 8H), 7.09-7.06 (m, 2H), 6.73 (s, 1H), 6.38-6.36 (d, 1H), 3.51 (s, 3H), 3.27-3.24 (m, 1H), 2.85-2.76 (m, 1H), 2.34-2.21 (m, 2H), 2.16 (s, 2H), 1.65-1.53 (d, 3H), 1.45 (s, 3H), 1.08 (s, 3H), 0.96 (s, 3H); LC-MS Method 2 tR=1.05 min, m/z=475.

Provenance & Evidence