Potassium Phosphate, Tribasic → HCID 89783825, compound

Participants

Reaction Conditions

Reaction Steps

Argon was bubbled into a mixture of potassium phosphate tribasic (0.26 g, 1.22 mmol), Xphos (Strem; 0.015 g, 0.030 mmol), Pd2dba3 (Strem; 0.014 g, 0.015 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) (0.32 g, 1.22 mmol), 8-bromo-2-(isopropylamino)-3-phenylquinazolin-4(3H)-one (402c, 0.109 g, 0.304 mmol) in 2 mL dioxane and 0.4 mL water for 2 min. The reaction was sealed and heated to 80° C. After 2 h the reaction was concentrated onto 1.5 g silica gel and dried. The material was 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 2-(isopropylamino)-8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)-3-phenylquinazolin-4(3H)-one (55 mg, 0.133 mmol, 43.7% yield) as a light-yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.15 (1H, br. s.), 8.03 (1H, dd, J=7.7, 1.5 Hz), 7.78 (1H, dd, J=7.7, 1.5 Hz), 7.52-7.66 (3H, m), 7.35-7.46 (2H, m), 7.17 (1H, t, J=7.7 Hz), 7.07 (1H, d, J=2.0 Hz), 6.94 (1H, s), 5.25 (1H, d, J=7.2 Hz), 4.13-4.28 (1H, m), 3.42 (2H, td, J=6.8, 2.3 Hz), 2.86 (2H, t, J=6.8 Hz), 1.20 (6H, d, J=6.5 Hz). m/z (ESI, +ve) 414.1 (M+H)+.

Provenance & Evidence