反応 #626474

反応方程式

but-1-yne

diisopropylamine

3,5-dibromopyridine

But-1-yne

→

title compound

収率 87.0%

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

収率 87.0%

溶媒

acetonitrile

EtOAc

反応条件

後処理

1. 1
   その他gently bubbled through anhydrous acetonitrile
2. 2
   温度cooled in an ice-water bath
3. 3
   その他The solvents were evaporated
4. 4
   その他the residue was purified by flash chromatography on silica (gradient elution 0-20% EtOAc in heptane)

実験手順

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.

出典