Potassium Phosphate, Tribasic → 5-Methyl-2-isopropyloxy-4-(pyridine-4-YL)-nitrobenzene

Temperature

120 °C

To a mixture of 1-bromo-5-isopropoxy-2-methyl-4-nitrobenzene (Step 2, 1 g, 3.65 mmol), pyridine-4-boronic acid (490 mg, 4 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (300 mg, 0.73 mmol) and potassium phosphate (1.55 g, 7.3 mmol) in mixed solvent of dioxane (15 mL) and water (7.5 mL) was added tris(dibenzylidene-acetone)dipalladium (0) (334 mg, 0.36 mmol). This mixture was sealed and purged with nitrogen for 3 minutes and then heated at 120° C. for 5 hours. The mixture was cooled to room temperature, filtered, and the filtrate was concentrated. After concentration, the crude product was purified with silica gel flash column chromatography (60% ethyl acetate in hexanes) to afford 4-(5-isopropoxy-2-methyl-4-nitrophenyl)pyridine a as yellow solid: ESMS m/z 273.2 (M+H+).

1. customThis mixture was sealed
2. custompurged with nitrogen for 3 minutes
3. temperatureThe mixture was cooled to room temperature
4. filtrationfiltered
5. concentrationthe filtrate was concentrated
6. concentrationAfter concentration
7. customthe crude product was purified with silica gel flash column chromatography (60% ethyl acetate in hexanes)

ORD record

ord-321c895a2ee94bc68f186878eb4ff69c

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08519129B2