Cesium carbonate → (S)-3-((S)-1-(4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one

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 (300 mg, 0.63 mmol) and 6-bromo-[1,2,4]triazolo[1,5-a]pyridine (149 mg, 0.75 mmol) in dry 1,4-dioxane (15 mL) were added 2M aq Cs2CO3 (2 mL) and Pd(PPh3)Cl2 (40 mg, 0.056 mmol). After addition, the mixture was heated to reflux for 2 h under N2 atmosphere. The solid was filtered off and diluted with water (50 mL) and EtOAc (100 mL), the mixture was extracted with EA (3×50 mL). The combined organic layer was washed with brine (100 mL), dried over Na2SO4, filtered, and concentrated to dryness. The residue was purified by prep TLC to afford (S)-3-((S)-1-(4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one (188 mg, yield: 63.5%). LC-MS Method tR=1.18 min, m/z=471, 418; 1H NMR (CDCl3): δ 1.05 (s, 3H), 1.12 (s, 3H), 1.49-1.51 (m, 3H), 2.15-2.18 (m, 2H), 2.21-2.23 (m, 1H), 2.32-2.37 (m, 1H), 2.82-2.87 (m, 1H), 3.01-3.06 (m, 1H), 5.63-5.68 (m, 1H), 7.01-7.06 (m, 2H), 7.19-7.22 (m, 3H), 7.29-7.32 (m, 3H), 7.33-7.36 (m, 2H), 7.36-7.38 (m, 1H), 7.75-7.78 (m, 1H), 7.11-7.13 (m, 1H), 8.79 (s, 1H).

Provenance & Evidence