Sodium Carbonate → HCID 50905956, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-(2-Hydroxy-2-methyl-propyl)-3-{1-methyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl}-6-phenyl-[1,3]oxazinan-2-one (50 mg, 151.5 μmol) in DME (10 mL) were added a solution of sodium carbonate (64.5 mg, 609 μmol) in EtOH (2 mL) and water (1 mL), 1-cyclopropyl-4-iodo-1H-pyridin-2-one (19 mg, 73 μmol) and Pd(PPh3)4(7.5 mg, 6 μmol) successively under nitrogen. The reaction mixture was stirred at 100° C. for 2.5 h and then 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 preparative prep HPLC to afford 3-{1-[4-(1-Cyclopropyl-2-oxo-1,2-dihydro-pyridin-4-yl)-phenyl]-1-methyl-ethyl}-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one (41 mg, 71%). 1H NMR (CDCl3) δ 7.45-7.25 (m, 8H), 7.12-7.10 (d, 2H), 6.75 (s, 1H), 6.40 (d, 1H), 3.39-3.29 (m, 2H), 2.90-2.83 (m, 1H), 2.39-2.21 (m, 4H), 1.67 (d, 3H), 1.50 (s, 3H), 1.16-1.12 (m, 5H), 1.02 (s, 3H), 0.92-0.87 (m, 2H); LC-MS Method 2 tR=1.10 min, m/z=501.

Provenance & Evidence