Methyl 4-bromobenzoate → HCID 22730763, Verbindung

Temperatur

90 °C

Toluene (20 mL), ethanol (6 mL), and water (2 mL) were added to commercially available 1-N—BOC-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine (1.00 g, 3.23 mmol), methyl 4-bromobenzoate (695 mg, 3.23 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy biphenyl (266 mg, 0.65 mmol), palladium(II) acetate (73 mg, 0.32 mmol), and tripotassium phosphate (2.06 g, 9.70 mmol) under nitrogen atmosphere, and the mixture was stirred at 90° C. for 5 hours. The reaction mixture was cooled to room temperature and a saturated aqueous sodium bicarbonate solution and ethyl acetate were added for partition. The aqueous layer was extracted with ethyl acetate three times and then the organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was evaporated and the resultant residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=19:1-13:7) to obtain the title compound (0.99 g, 96%).

1. temperatureThe reaction mixture was cooled to room temperature
2. customfor partition
3. extractionThe aqueous layer was extracted with ethyl acetate three times
4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
5. filtrationfiltered
6. customThe solvent was evaporated
7. customthe resultant residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=19:1-13:7)

ORD-Eintrag

ord-2ec424bbd8e84c82b376f7a6194b340a

Quelldatensatz

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08933099B2