1-(6-ETHYNYL-PYRIDIN-2-YL)-ETHANONE synthesis

4synthesis methods

Product Name:1-(6-ETHYNYL-PYRIDIN-2-YL)-ETHANONE
CAS Number:874379-35-8
Molecular formula:C9H7NO
Molecular Weight:145.158

Ethanone, 1-[6-[2-(trimethylsilyl)ethynyl]-2-pyridinyl]-

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Yield:874379-35-8 402 mg

Reaction Conditions:

with methanol;potassium carbonate at 20; for 2 h;

Steps:

Method M. l-(6-ethyny]pyridin-2-yl)ethan-l-one

Method M. l-(6-ethyny]pyridin-2-yl)ethan-l-one l-(6-bromopyridin-2-yl)ethan-l-one (l .Og. 5.0mmol, leq), Cul (38mg, 0.2mmol, 0.04 eq), PdCl₂(PPh₃)₂ (140mg, 0.2mmol, 0.04 eq) in THF (10ml), TEA (1.5ml) was degassed under bubbling nitrogen for 10 min. To this solution was added TMS-acetylene (1.42 ml, 10 mmol, 2 eq) and the reaction was stirred for 2 hours at RT. The reaction was diluted in hexanes and filtered over a plug of silica gel to remove the majority of impurities. The eluent was concentrated under reduced pressure and further purified by silica gel chromatography (5% EtOAc/Hexanes) to afford l-(6-((trimethylsilyl)ethynyl)pyridin-2-yl)ethan-l-one (1.09g) as a yellow oil that was used without further purification. To a solution of l-(6- ((trimethylsilyl)ethynyl)pyridin-2-yl)ethan-l -one (crude from previous reaction) in methanol (20ml) was added a large excess of potassium carbonate. The reaction was stirred 2 hours at RT and concentrated under reduced pressure. The concentrate was partitioned in DCM/water, extracted 2 x DCM, dried over sodium sulfate and concentrated. The crude product was purified by silica gel chromatography to give l-(6-ethynylpyridin-2-yl)ethan-l -one (402 mg, 55% yield over 2 steps) as a white solid.

References:

WO2016/123253,2016,A1 Location in patent:Page/Page column 32

Ethanone, 1-[6-(3-hydroxy-3-methyl-1-butyn-1-yl)-2-pyridinyl]-

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References

49669-13-8 Synthesis

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626-05-1 Synthesis

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References