Sodium Carbonate → HCID 118497072, Verbindung

Temperatur

80 °C

To a solution of methyl 2-chloro-4-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1.67 g, 5.30 mmol) in THF (10 mL) was added 2-bromo-3-fluoropyridine (933 mg, 5.30 mmol), tri(o-tolyl)phosphine (67 mg, 0.22 mmol), Na2CO3 (2.25 g, 21.2 mmol) and water (1.6 mL) and the reaction was purged with nitrogen for 15 minutes. Bis(dibenzylidene acetone)palladium (63 mg, 0.11 mmol) was added with further purging with nitrogen for 10 minutes before heating at 80° C. for 1 hour. The reaction was cooled to room temperature and filtered through a pad of arbocel, washing through with EtOAc (50 mL). The filtrate was washed with water (50 mL), dried over magnesium sulfate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 10-20% EtOAc in heptanes to afford the title compound (240 mg, 21%).

1. customthe reaction was purged with nitrogen for 15 minutes
2. customwith further purging with nitrogen for 10 minutes
3. temperatureThe reaction was cooled to room temperature
4. filtrationfiltered through a pad of arbocel
5. washwashing through with EtOAc (50 mL)
6. washThe filtrate was washed with water (50 mL)
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated in vacuo
9. customThe residue was purified
10. washeluting with 10-20% EtOAc in heptanes

ORD-Eintrag

ord-f8344bf7f30c485381b699bf797e9c93

Quelldatensatz

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09328096B2