Potassium Phosphate, Dibasic → HCID 89783907, compound

Participants

Reaction Steps

Argon was bubbled into a slurry of potassium phosphate dibasic (Aldrich; 0.164 g, 0.944 mmol), 1,1-bis[(di-t-butyl-p-methylaminophenyl]palladium(ii) chloride (Aldrich; 0.019 g, 0.027 mmol), 3-fluoro-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline (618) (0.155 g, 0.539 mmol), (R)-2-bromo-6-methyl-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (287) (0.058 g, 0.270 mmol) in 1.5 mL DMF and 0.5 mL water for 1 min. The reaction was sealed and placed in a 70° C. oil bath for 45 min. Additional 1 equiv boronic ester and 5 mg catalyst added, and the reaction was heated 30 min additional. The reaction was partitioned between water and EtOAc. The aq. layer was extracted 1× EtOAc, and the combined organic layers were washed with water 2 times, saturated aq. NaCl once, and the organics were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The material was treated with DCM and purified by silica gel chromatography (24 g column) using 0-100% 90/10 DCM/MeOH in DCM. The product-containing fractions were concentrated to afford (R)-2-(3-fluoro-2-methylquinoxalin-5-yl)-6-methyl-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (287f; 0.034 g, 0.115 mmol, 42% yield) as a orange solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.90 (1H, s), 8.07 (1H, d, J=7.6 Hz), 7.94 (1H, d, J=8.2 Hz), 7.78-7.88 (1H, m), 7.69 (1H, s), 7.01 (1H, d, J=1.6 Hz), 4.58 (1H, q, J=6.7 Hz), 2.71 (3H, s), 1.41 (3H, d, J=6.7 Hz). m/z (ESI, +ve) 297.0 (M+H)+.

Provenance & Evidence