Reaction #1528432

Reaction equation

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

potassium carbonate

DME

→

solid

Yield 90.0%

8-ethenyl-7-fluoro-2-(methyloxy)-1,5-naphthyridine

Yield 90.0%

Solvents

H2O

Conditions

Workup

1. 1
   Otherthe reaction contents
2. 2
   Concentrationwere concentrated
3. 3
   Otherthe product purified by chromatography on silica gel (hexanes/EtOAc, 4:1)

Procedure

To a solution of 8-bromo-7-fluoro-2-(methyloxy)-1,5-naphthyridine (2.0 g, 7.81 mmol), potassium carbonate (1.08 g, 7.81 mmole), tetrakis-triphenylphosphine (90 mg, 0.08 mmole) in DME (60 mL) and H2O (20 mL) was added 2,4,6-trivinylcycloborane-pyridine complex (0.94 g, 3.91 mmole). After stirring for 10 hours at 85° C. the reaction contents were concentrated and the product purified by chromatography on silica gel (hexanes/EtOAc, 4:1) to give a low melting solid (1.43 g, 90%).

Source