Cesium carbonate → HCID 44194658, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-4-(2-hydroxy-2-methylpropyl)-4-phenyl-1-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)piperidin-2-one (20 mg, 0.042 mmol) and 4-iodo-1-methylpyridin-2(1H)-one (7.8 mg, 0.084 mmol) in dry 1,4-dioxane (5 mL) was added Cs2CO3 (0.042 mL, 0.084 mmol) and Pd(PPh3)2Cl2 (10 mg). After addition, the mixture was warmed at 110° C. for 2 h under nitrogen. After TLC showed the starting material had disappeared, the solid was filtered off. Water (20 mL) and EtOAc (10 mL) were added, the organic layer was separated, and the aqueous layer was extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to give 4-(4-((S)-1-((R)-4-(2-hydroxy-2-methylpropyl)-2-oxo-4-phenylpiperidin-1-yl)ethyl)phenyl)-1-methylpyridin-2(1H)-one (2.63 mg, 14%), which was purified by preparative HPLC. LC-MS Method 2, tR=1.163 min, m/z=459.2. 1H NMR (CDCl3): δ 0.81 (s, 3H), 0.98 (s, 3H), 1.41 (d, 3H), 1.80 (m, 1H), 1.96 (m, 1H), 1.99-2.18 (m, 4H), 2.58 (m, 1H), 2.87 (m, 1H), 3.47 (m, 1H), 3.57 (s, 3H), 5.95 (m, 1H), 6.41 (m, 1H), 6.80 (s, 1H), 6.91 (m, 2H), 7.18 (m, 1H), 7.24 (m, 6H), 7.32 (d, 1H).

Provenance & Evidence