Potassium Carbonate → HCID 15325851, compound

Temperature

80 °C

A flask was charged with (1-methyl-6-oxo-1,6-dihydropyridin-3-yl)boronic acid (80 mg, 0.52 mmol), potassium carbonate (217 mg, 1.57 mmol), and 1,1-bis(diphenylphosphino)ferrocenedichloropalladium(II) (19 mg, 0.026 mmol) and evacuated and purged with argon (5×). 2,6-Dibromopyridine (130 mg, 0.55 mmol) was placed into a separate flask and evacuated and backfilled with argon (3×). Degassed dimethylformamide (3.6 mL) was added to the vial containing 2,6-dibromopyridine and the solution was transferred to the flask containing the remainder of the reactants. The mixture was heated at 80° C. overnight, then cooled to room temperature, taken up in water, and extracted with ethyl acetate (2×). The ethyl acetate layers were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting mixture was purified via silica gel chromatography (0-5% methanol in ethyl acetate) to afford the title compound.

1. customevacuated
2. custompurged with argon (5×)
3. customevacuated
4. additionDegassed dimethylformamide (3.6 mL) was added to the
5. additionvial containing 2,6-dibromopyridine
6. additioncontaining the remainder of the reactants
7. temperaturecooled to room temperature
8. extractionextracted with ethyl acetate (2×)
9. dry with materialdried over magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure
12. customThe resulting mixture was purified via silica gel chromatography (0-5% methanol in ethyl acetate)

ORD record

ord-fc98d60b0cef4308a24443e61eeb7b86

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367706B2