Potassium Acetate → HCID 86700866, compound

Temperature

115 °C

A flask was charged with 2-(4-chlorophenyl)-5-nitropyridine (4.48 g, 14.26 mmol), pinoco boronate (14.48 g, 57.0 mmol), potassium acetate (5.59 g, 57.0 mmol), Pd-(Xphos) (1.404 g, 1.900 mmol), X-phos (1.359 g, 2.85 mmol) and dioxane (50 ml) at room temperature. The flask was sealed, flushed with nitrogen for three times and heated at 115° C. for 72 hours. The mixture was cooled down to room temperature and diluted with dioxane (50 ml) and EtOAc (100 ml), filtered and the filtrate was concentrated. The residue was added dioxane (30 ml) and filtered, the filtrate was purified by flash chromatography (heptanes/acetone 1/2) to afford 5-nitro-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine (3.9 g, 84%) as yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) ppm 1.37 (s, 9H) 7.43-8.15 (m, 7H).

1. customThe flask was sealed
2. customflushed with nitrogen for three times
3. temperatureThe mixture was cooled down to room temperature
4. additiondiluted with dioxane (50 ml) and EtOAc (100 ml)
5. filtrationfiltered
6. concentrationthe filtrate was concentrated
7. additionThe residue was added dioxane (30 ml)
8. filtrationfiltered
9. customthe filtrate was purified by flash chromatography (heptanes/acetone 1/2)

ORD record

ord-a6617b4382e14a40885a603ee0e7e84d

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08993619B2