Reaction #156328

Reaction equation

5-Bromo-4-fluoro-pyridin-2-ylamine mono HCl salt

tributyl(vinyl)stannane

tributyl(vinyl)stannane

→

title product

4-Fluoro-5-vinyl-pyridin-2-ylamine

Solvents

dioxane

EtOAc

Conditions

Workup

1. 1
   Washwashed with brine
2. 2
   Dryingdried over Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Otherevaporated to dryness
5. 5
   OtherThe residue was purified by chromatography with hexane and EtOAc

Procedure

5-Bromo-4-fluoro-pyridin-2-ylamine mono HCl salt (xvii) (368 mg, 1.62 mmol), tributyl(vinyl)stannane (0.52 mL, 1.78 mmol) and palladium tetrakis(triphenylphosphine) (19 mg, 0.016 mmol) in dioxane (6 mL) under argon were heated under microwave irradiation at 120° C. for 45 min. Were then added tributyl(vinyl)stannane (0.2 mL, 0.685 mmol) and palladium tetrakis(triphenylphosphine) (7 mg, 0.006 mmol) and the RM was placed under argon and heated once more under microwave irradiation at 120° C. for 45 min. The RM was diluted with EtOAc and washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by chromatography with hexane and EtOAc to yield the title product as a yellow solid (tR 1.76 min (conditions 8), MH+=139).

Source