Sodium Carbonate → HCID 58438484, compound

Participants

Reaction Steps

To a 100 mL round-bottomed flask was added 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indan-1-one (SM-1a, 1.50 g, 5.81 mmol), 2-chloro-5-methylpyrimidine (747 mg, 5.81 mmol), sodium carbonate (2.47 g, 23.3 mmol), 27 mL of dioxane, and 3 mL of water. The mixture was degassed with nitrogen for 15 minutes. Palladium tetrakis(triphenylphosphine) (356 mg, 0.31 mmol) was added and the mixture was degassed with nitrogen for an additional 15 minutes. The reaction was heated at reflux overnight. The reaction was cooled to room temperature and was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and concentrated. The final product was purified by silica chromatography on a Combiflash ISCO purification system (Teledyne Isco Inc., Lincoln, Nebr.) eluting with 20-35% ethyl acetate in heptanes to provide a white solid (SM-1d, 1.12 g, 86%). MS (ES+) 225.2 (M+H+). 1H NMR (CDCl3) δ 2.38 (s, 3H), 2.74-2.78 (m, 2H), 3.23 (t, 2H), 7.85 (d, 1H), 8.44 (d, 1H), 8.53 (s, 1H), 8.68 (s, 2H).

Provenance & Evidence