Nitrogen → HCID 59402315, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of benzyl 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate (78.5 mg, 0.230 mmol), 4-(7-bromo-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine (0.080 g, 0.19 mmol) (Peak 1, Example 49, Step 7), dichloro(bis{di-tert-butyl[4-(dimethylamino)phenyl]phosphoranyl})palladium (4.07 mg, 0.00575 mmol), and sodium carbonate (0.0406 g, 0.383 mmol) in 1,4-dioxane (0.88 mL) and water (0.1 mL) was vacuumed and refilled with N2 for 3 times and then stirred at 90° C. overnight. LCMS monitored reaction. After cooling down to r.t., the mixture was diluted with ethyl acetate, washed with water and brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography on a silica gel column with methanol in methylene chloride (0-10%) to afford the desired product. LCMS (M+H)+: m/z=552.1.

Provenance & Evidence