Sodium Carbonate → HCID 59436008, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-[(2,6-dichloro-4-iodophenyl)amino]pyrido[4,3-c]-1,6-naphthyridin-10(9H)-one (Example 156, Step 1) (30 mg, 0.06 mmol) in DMF (1.5 mL) were added sodium carbonate (2 M, 0.5 mL), tetrakis(triphenylphosphine)palladium (0) (14.3 mg, 0.12 mmol), and (3E)-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol (13.2 mg, 0.06 mmol). The solution was degassed by bubbling nitrogen gas and heated to 80° C. overnight. After cooling to room temperature, the mixture was extracted with 3:1 CHCl3/iPrOH. The organic layers were combined, dried with MgSO4, filtered, and concentrated under reduced pressure. Purification by column chromatography on silica gel (100% CH2Cl2 to 70% CH2Cl2/30% MeOH) afforded the title compound.

Provenance & Evidence