Cesium carbonate → 2-(6-tert-Butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-6-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-benzaldehyde

Participants

Reaction Steps

88 mg (0.20 mmol) of 1-methyl-3-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyridin-2-one and 81 mg (0.20 mmol) of 2-bromo-6-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-benzaldehyde were weighed into a 4 mL reaction vial fitted with a stir bar and septum cap. Added 2 mL of dioxane. Added 222 μL of an 0.88 mg/μL solution of cesium carbonate in water. Added 7.8 mg (0.0096 mmol) of [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride 1:1 complex with dichloromethane. The reaction was sparged with nitrogen for 5 min. Sealed the vial with a cap and stirred at 100° for 60 min. Poured the reaction mixture into 10 mL CH2Cl2 and 10 mL water. Separated phases and extracted the aqueous phase with 5 mL CH2Cl2. Combined the organic extracts, dried over Na2SO4 and removed the solvent on rotavap. Purified by silica gel flash chromatography using gradient elution with 100% hexane to 100% 5:6:1 hexane:CH2Cl2:2-PrOH. Recrystallized the product from 2-PrOH. Dried under high vacuum at 120° overnight to obtain 77 mg of the title compound as a pale yellow solid. MS (ESI) 637 (M+H)+.

Provenance & Evidence