Reaktion #43412

Reaktionsgleichung

Potassium carbonate

water

pyridine tris(1-methylethenyl)boroxin

water

8-bromo-3,7-difluoro-2-(methyloxy)-1,5-naphthyridine

→

3,7-Difluoro-8-(1-methylethenyl)-2-(methyloxy)-1,5-naphthyridine

Lösungsmittel

ether

dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturto reflux for 5 hours
3. 3
   SonstigeThe phases were separated
4. 4
   Extraktionthe aqueous phase further extracted with ether (2×200 ml)
5. 5
   TrocknenThe combined organic extracts were dried over magnesium sulphate
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe residue was chromatographed on silica eluting with a gradient of 0-50% ethyl acetate in hexane affording a white solid (820 mg, 84%)

Vorschrift

A solution of 8-bromo-3,7-difluoro-2-(methyloxy)-1,5-naphthyridine (1.14 g, 4.15 mmol) and tetrakis(triphenylphosphine)palladium(0) (240 mg, 0.21 mmol) in degassed dimethoxyethane (40 ml) was stirred under argon for 30 minutes. Potassium carbonate (570 mg, 4.2 mmol), water (12 ml) and pyridine-tris(1-methylethenyl)boroxin (1:1) (470 mg, 1.66 mmol) were added the mixture was heated to reflux for 5 hours. The cooled mixture was treated with water (100 ml) and ether (200 ml). The phases were separated and the aqueous phase further extracted with ether (2×200 ml). The combined organic extracts were dried over magnesium sulphate and evaporated. The residue was chromatographed on silica eluting with a gradient of 0-50% ethyl acetate in hexane affording a white solid (820 mg, 84%).

Quelle