Sodium Carbonate → 4-(1-((9-methyl-6-morpholino-2-(1-(phenylsulfonyl)-1H-indol-3-yl)-9H-purin-8-yl)methyl)piperidin-4-yl)morpholine

Participants

Reaction Conditions

Reaction Steps

To a degassed suspension of 4-(1-((2-chloro-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperidin-4-yl)morpholine (249 mg, 0.571 mmol), 1-(phenylsulfonyl)-3-indoleboronic acid (189 mg, 0.628 mmol), 2M Na2CO3 aqueous solution (0.571 mL, 1.0 mmol) in toluene (5 mL) and ethanol (2 mL) was added Pd(PPh3)4 (33 mg, 0.029 mmol). The suspension was then stirred under nitrogen at 100° C. for 18 hours. The reaction mixture was then diluted with EtOAc and water. The layers were separated. The aqueous layer was extracted three times with EtOAc. The combined organic extracts were washed with water, dried over Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography (25% MeOH in DCM) to give the title compound as a white solid (357 mg, 95.2%). LCMS: M+H+=657.2.

Provenance & Evidence