반응 #626474

반응 방정식

but-1-yne

diisopropylamine

3,5-dibromopyridine

But-1-yne

→

title compound

수율 87.0%

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

수율 87.0%

용매

acetonitrile

EtOAc

반응 조건

후처리

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

실험 절차

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.

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