Sodium Carbonate → HCID 21956061, compound

Temperature

105 °C

To a solution of 6-amino-2-bromo-5-nitropyridine (2.0 g, 9.2 mmol) and 2-fluorophenylboronic acid (2.57 g, 18 mmol) in dimethoxyethane (60 mL) were added 2M aqueous sodium carbonate solution (18 mL) and tetrakistriphenylphosphine palladium(0) (106 mg, 0.092 mmol). The mixture was stirred at 105° C. for 16 hours under a nitrogen atmosphere. After the reaction mixture was cooled to room temperature, it was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was dissolved in a mixture of ethyl acetate (30 mL) and methanol (30 mL). To the solution was added 10% palladium carbon (200 mg), and the mixture was stirred at room temperature for 14 hours under a hydrogen atmosphere. After removal of the palladium catalyst by filtration, the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (chloroform:methanol=30:1) to give the title compound (1.87 g, 100%) as a reddish brown oil.

1. temperatureAfter the reaction mixture was cooled to room temperature
2. extractionit was extracted with ethyl acetate
3. washThe organic layer was washed with saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. concentrationconcentrated in vacuo
6. dissolutionThe residue was dissolved in a mixture of ethyl acetate (30 mL) and methanol (30 mL)
7. additionTo the solution was added 10% palladium carbon (200 mg)
8. stirringthe mixture was stirred at room temperature for 14 hours under a hydrogen atmosphere
9. customAfter removal of the palladium catalyst
10. filtrationby filtration
11. concentrationthe filtrate was concentrated in vacuo
12. customThe residue was purified by silica gel column chromatography (chloroform:methanol=30:1)

ORD record

ord-affd993f060340d5ae2e64d5427f597d

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105526B2