Potassium Acetate → (3-Bromo-5-hydroxy-phenyl)-pyridin-3-yl-methanone

Temperature

80 °C

A 50 mL tube was charged with (3,5-dibromo-phenyl)-pyridin-3-yl-methanone (2.55 g, 7.5 mmol), bis(pinacolato)diboron (1.26 g, 5.0 mmol), potassium acetate (1.47 g, 15.0 mmol) and Pd(dppf)Cl2.CH2Cl2 (200 mg). DMSO (15 mL) was added, and the solution was degassed with nitrogen, then the tube was sealed. After heating the tube for 16 h at 80° C., the mixture was diluted with ethyl acetate (10 mL) and extracted with brine (10 mL, three times), and saturated sodium bicarbonate (5 mL), and the organic layer was dried. To a solution of the crude product prepared above in acetone (20 mL) was added an aqueous solution of Oxone (6.15 g in 30 mL water), and the reaction mixture was stirred vigorously for 10 min at room temperature. The reaction was quenched with aqueous sodium hydrogen sulfite. The brown solution was extracted with ethyl acetate, and the organic layer was extracted with brine followed by water, then dried and concentrated. The residue was passed through a short pad of Silica gel column using a gradient of 2% MeOH in methylene chloride to 4% MeOH in methylene chloride as an eluent to give (3-bromo-5-hydroxy-phenyl)-pyridin-3-yl-methanone (800 mg, 2.87 mmol, 57%) as a foam.

1. customthe solution was degassed with nitrogen
2. customthe tube was sealed
3. additionthe mixture was diluted with ethyl acetate (10 mL)
4. extractionextracted with brine (10 mL, three times), and saturated sodium bicarbonate (5 mL)
5. customthe organic layer was dried
6. customTo a solution of the crude product prepared above in acetone (20 mL)
7. customThe reaction was quenched with aqueous sodium hydrogen sulfite
8. extractionThe brown solution was extracted with ethyl acetate
9. extractionthe organic layer was extracted with brine
10. customdried
11. concentrationconcentrated

ORD record

ord-ce2eec77f655423d968bc41519cfb9aa

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07504401B2