Sodium Carbonate → HCID 117993113, compound

Participants

Reaction Conditions

Reaction Steps

To a vessel containing (R)-3-(6-chloro-2-methoxypyridin-3-yl)-3-methylpiperidin-2-one (80 mg, 0.31 mmol), 1-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (105 mg, 0.41 mmol), dioxane (3 mL), and 2 M Na2CO3 (0.31 mL, 0.63 mmol) was added Pd(dppf)Cl2 (23 mg, 0.031 mmol). The reaction was stirred for 18 h at 110° C. The mixture was diluted with ethyl acetate (50 mL) and washed with brine (15 mL). The organic layer was dried over Na2SO4, filtered, and concentrated to provide a crude product. Purification by preparative TLC (100% Ethyl Acetate) provided the title compound (80 mg, 76%). 1H NMR (400 MHz, CDCl3) δ: 1.65-1.70 (m, 1H); 1.72 (s, 3H), 1.78-1.84 (m, 1H), 1.95-2.05 (m, 1H), 2.40 (td, 1H), 3.35-3.41 (m, 1H), 3.52 (td, 1H), 3.87 (s, 3H), 4.11 (s, 3H), 5.83 (br. s., 1H), 6.49 (d, 1H), 7.10 (d, 1H), 7.41 (d, 1H), 7.64-7.67 (m, 2H), 7.77 (dd, 1H), 8.03 (s, 1H).

Provenance & Evidence