Réaction #626474

Équation de réaction

but-1-yne

diisopropylamine

3,5-dibromopyridine

But-1-yne

→

title compound

Rendement 87.0%

3-Bromo-5-(but-1-ynyl)-pyridine

Rendement 87.0%

Solvants

acetonitrile

EtOAc

Conditions de réaction

Traitement

1. 1
   Autregently bubbled through anhydrous acetonitrile
2. 2
   Températurecooled in an ice-water bath
3. 3
   AutreThe solvents were evaporated
4. 4
   Autrethe residue was purified by flash chromatography on silica (gradient elution 0-20% EtOAc in heptane)

Mode opératoire

But-1-yne (g) was during 5 min gently bubbled through anhydrous acetonitrile cooled in an ice-water bath. The resulting solution contained about 170 mg but-1-yne per mL. The solution of but-1-yne (4.57 mL, 14.36 mmol) and diisopropylamine (3.72 mL, 26.11 mmol) were added sequentially to a mixture of 3,5-dibromopyridine (3.09 g, 13.06 mmol), bis(triphenylphosphine)-palladium(IT) chloride (0.458 g, 0.65 mmol) and CuT (0.249 g, 1.31 mmol) in acetonitrile (15 mL) under an argon atmosphere. The resulting mixture was stirred at r.t. overnight, diluted with EtOAc and passed through a short plug of silica. The solvents were evaporated and the residue was purified by flash chromatography on silica (gradient elution 0-20% EtOAc in heptane) to give 2.40 g of the title compound (87% yield): 1H NMR (500 MHz, DMSO-d6) δ ppm 1.17 (t, 4 H), 2.47 (q, 3 H), 8.11 (t, 1 H), 8.57 (d, 1 H), 8.65 (d, 1 H); MS (ES+) m/z 210 [M+H]F.

Source