Sodium Carbonate → HCID 44594889, compound

Participants

Reaction Steps

To a stirred solution of 2,2-dimethyl-5-oxo-4-(4-(quinolin-2-ylmethoxy)phenyl)-2,5-dihydro-1H-pyrrol-3-yl trifluoromethanesulfonate (500 mg, 1.01 mmol) in 1,4-dioxane (20 mL) were added 4-methoxyphenylboronic acid (185 mg, 1.2 mmol), Na2CO3 (256 mg, 3.04 mmol) and water (4 mL) at RT under an inert atmosphere. The mixture was stirred for 30 min and then Pd(PPh3)4 (117 mg, 0.1 mmol) was added. Stirring was continued at 80° C. for 16 h. The reaction mixture was then diluted with water and extracted with EtOAc (2×200 mL). The combined organic layers were washed with water and brine, and then dried over Na2SO4 and concentrated in vacuo to afford 4-(4-methoxyphenyl)-5,5-dimethyl-3-(4-(quinolin-2-ylmethoxy)phenyl)-1H-pyrrol-2(5H)-one (30 mg, 7%) as a white solid. 1H NMR (500 MHz, CDCl3): δ 8.20-8.01 (m, 2H), 7.87-7.62 (m, 2H), 7.61-7.51 (m, 2H), 7.38-7.30 (m, 2H), 7.16-7.09 (m, 2H), 6.91 6.80 (m, 4H), 5.96 (bs, 1H), 5.39 (s, 2H), 3.81 (s, 3H), 1.43 (s, 6H). MS: M+H: m/z=451.2 and HPLC: 94%, (Condition-I).

Provenance & Evidence