Potassium Phosphate, Tribasic → HCID 89783385, compound

Participants

Reaction Conditions

Reaction Steps

Argon was bubbled into a mixture of potassium phosphate tribasic (0.28 g, 1.02 mmol), Xphos (Strem, 0.012 g, 0.026 mmol), Pd2dba3 (Strem; 0.012 g, 0.013 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (609) (0.201 g, 0.766 mmol), 8-bromo-2-(2,6-dimethylphenyl)quinoxaline (401a; 0.08 g, 0.255 mmol) in 2 mL dioxane and 0.4 mL water for 2 min. The reaction was sealed and heated to 80° C. After 3 h, the reaction was cooled and 1.6 g silica gel was added, and the material dried in vacuo. The material was purified by silica gel chromatography (24 g ISCO gold column) using 0-50% 90/10 DCM/MeOH in DCM. The product-containing fractions were concentrated to afford 2-(3-(2,6-dimethylphenyl)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (0.055 g, 0.149 mmol, 58% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.77 (1H, br. s.), 8.97 (1H, s), 8.14 (1H, dd, J=7.3, 1.3 Hz), 7.95-8.02 (1H, m), 7.86-7.94 (1H, m), 7.31-7.39 (1H, m), 7.21-7.31 (3H, m), 6.98 (1H, s), 3.40 (2H, td, J=6.8, 2.3 Hz), 2.85 (2H, t, J=6.8 Hz), 2.10 (6H, s). m/z (ESI, +ve) 369.0 (M+H)+.

Provenance & Evidence