Potassium Carbonate → HCID 66809318, compound

Participants

Reaction Steps

A solution containing 64 (5 g, 0.011 mol), n-Bu4NCl (3.3 g, 0.012 mol), K2CO3 (1.65 g, 0.012 mol), and NaHCO2 (0.81 g, 0.012 mol) in DMF (20 mL) was degassed under high vacuum. Palladium acetate (0.49 g, 0.002 mol) was added and the heterogeneous reaction mixture was immersed in a preheated (80-85° C.) oil bath. After 3 h, TLC analysis revealed complete consumption of 64 [1:1 hexane/EtOAc, Rf(64)=0.4, Rf(65)=0.5]. The reaction mixture was cooled in an ice bath and diethyl ether (100 mL) was added. The mixture was filtered through Celite® and the solids were washed with diethyl ether. The filtrate was washed with water, brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by normal phase HPLC (10-100% EtOAc/hexane over 50 min) to afford 2.2 g (54%) of 65 as brown, viscous oil. 1H NMR (CDCl3, 300 MHz) δ8.22-8.1 (m, 1H), 7.7-7.5 (m, 1H), 7.15-6.97 (m, 2H), 3.8-2.65 (m, 4H), 2.6 (s, 3H), 2.12-1.85 (m, 1H), 1.62 (s, 1H), 1.42 (s, 9H, major rotamer), 1.4 (s, minor rotamer), 0.9 (d, J=6 Hz, 3H) ppm. Mass spectrum, m/z=274.5 (M-BOC)+.

Provenance & Evidence