Ethyl Acetate → HCID 58485318, compound

Participants

Reaction Steps

To a solution of (S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one (20 mg, 0.041 mmol), 5-bromo-2-(2-fluoroethoxy)pyridine (9.2 mg, 0.041 mmol), and 2 N aq Cs2CO3 (0.2 mL, 0.41 mmol) in 1,4-dioxane (2 mL) was added Pd(PPh3)2Cl2 (3 mg, 0.0041 mmol) under N2. The mixture was refluxed for 2 h under N2, treated with EtOAc (10 mL) and water (10 mL). The organic layer was dried over Na2SO4 and concentrated. The residue was purified by preparative HPLC to give (S)-3-((S)-1-(4-(6-(2-fluoroethoxy)pyridin-3-yl)phenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one (2.20 mg, 11%). LC-MS Method 2 tR=1.21 min, m/z=515, 493; 1H NMR (CD3OD): δ 0.95 (s, 3H), 1.26 (s, 3H), 1.54 (d, 3H), 2.15 (s, 2H), 2.21 (m, 1H), 2.46 (m, 2H), 3.02 (m, 1H), 4.50 (t, 1H), 4.57 (t, 1H), 4.66 (t, 1H), 4.79 (t, 1H), 5.57 (q, 1H), 6.88 (d, 1H), 7.02 (d, 2H), 7.31 (m, 7H), 7.85 (dd, 1H), 8.25 (d, 1H).

Provenance & Evidence