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Method for synthesizing 2-carbonyl thienopyridine compound

A technology of phenopyridine and synthesis method, which is applied in the synthesis field of 2-carbonylthienopyridine compounds, can solve the problems of expensive starting materials, low atom economy and high synthesis cost, and achieves economical cost saving and product yield. The effect of high rate and few reaction steps

Inactive Publication Date: 2018-12-21
WUYI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in these reported methods, the starting materials are expensive, multi-step synthesis strategies are required, and the introduction of directing groups and subsequent removal are often required. The atom economy is not high, and the synthesis cost is high.

Method used

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  • Method for synthesizing 2-carbonyl thienopyridine compound
  • Method for synthesizing 2-carbonyl thienopyridine compound
  • Method for synthesizing 2-carbonyl thienopyridine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] This example is the synthesis of 1-(thien[2,3-b]2-pyridyl)ethanone.

[0025]

[0026] (a) Take a reaction tube, add 33mmg (0.20mmol) of 2-fluoro-3-(3-hydroxy)but-1-ynepyridine, 64mg (0.40mmol) of potassium ethyl xanthate, and 13mmg of copper diacetylacetonate (0.05mmol), dimethyl sulfoxide 3mL, stirred at 100°C for 12 hours, after the reaction was completed, 10mL of ethyl acetate was added to quench the reaction, and 5mL of saturated brine was added to wash, the organic phase was separated, and the aqueous phase was washed with ethyl acetate Extracted 3 times (the amount of ethyl acetate each time was 5mL) and combined the organic phases, added anhydrous sodium sulfate to dry, removed the solvent by distillation under reduced pressure, and separated by column chromatography to obtain the target product 1-(thiophene[2,3-b ]2-pyridyl)ethanone, the yield is 93%.

[0027] (b) Take a reaction tube, add 33.0mmg (0.20mmol) of 2-fluoro-3-(3-hydroxy)but-1-ynepyridine, 64mmg ...

Embodiment 2

[0031] This example is the synthesis of phenyl(thien[2,3-b]2-pyridyl)methanone.

[0032]

[0033] Take a reaction tube, add 239mmg (1.05mmol) of 3-(2-fluoro-3-pyridyl)-1-phenylpropan-2-yn-1-ol and 320mmg (2.00mmol) of potassium ethyl xanthate respectively , 26 mmg (0.10 mmol) of copper diacetylacetonate, 3 mL of dimethyl sulfoxide, and stirred at 100° C. for 12 hours. At the end of the reaction, add 10 mL of ethyl acetate to quench the reaction, add 5 mL of saturated brine to wash, separate the organic phase, and then extract the aqueous phase with ethyl acetate for 3 times (the amount of ethyl acetate each time is 5 mL) to combine the organic phases, add anhydrous Dry over sodium sulfate, remove the solvent by distillation under reduced pressure, and separate by column chromatography to obtain the target product, phenyl(thiophene[2,3-b]2-pyridyl)methanone, with a yield of 88%.

[0034] The characterization data is 1 H NMR (400MHz, CDCl 3 )δ8.71(dd, J=4.5,1.4Hz,1H),8.16(...

Embodiment 3

[0036] This example is the synthesis of 1-(thien[2,3-b]2-pyridyl)propan-1-one.

[0037]

[0038] In the reaction tube, add 1-(2-fluoro-3-pyridyl)-pent-1-yn-3-ol 179mmg (1.00mmol), potassium ethyl xanthate 320mmg (2.00mmol), diacetylacetone 26 mmg (0.10 mmol) of copper and 3 mL of dimethyl sulfoxide were stirred and reacted at 100° C. for 12 hours. After the reaction was completed, 10 mL of ethyl acetate was added to quench the reaction, and 5 mL of saturated brine was added for washing. Dry over sodium sulfate, remove the solvent by distillation under reduced pressure, and separate by column chromatography to obtain the target product 1-(thien[2,3-b]2-pyridyl)propan-1-one with a yield of 93%.

[0039] The characterization data is 1 H NMR (400MHz, CDCl 3 )δ8.67(s,1H),8.16(d,J=8.1Hz,1H),7.88(s,1H),7.36(dd,J=8.0,4.6Hz,1H),3.04(q,J=7.3 Hz,2H),1.28(t,J=7.3Hz,3H); 13 C NMR (100MHz, CDCl 3 )δ195.1, 163.3, 149.5, 143.2, 133.4, 132.7, 125.9, 120.2, 32.5, 8.3. GC-MS (EI, 70eV) ...

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Abstract

The invention discloses a method for synthesizing 2-carbonyl thienopyridine compound. According to the method provided by the invention, 2-halo-3-alkynol pyridine as shown in formula (I) and sulfur sources are mixed; and with the aid of a catalyst, after reacting in a solvent for a while, 2-carbonyl thienopyridine compound as shown in formula (II) is prepared after purification treatment. The sulfur sources are selected from one or more of elemental sulphur, ammonium sulfide, thiourea, sodium sulfide, and ethyl potassium xanthate, and the catalyst is selected from one of copper acetate, cuprous iodide, cuprous bromide, cuprous chloride, copper chloride, cupric acetylacetonate, palladium chloride, and copper trifluoromethanesulfonate. The technical scheme of the invention has the advantagesof less reaction steps, simple operation method, wide source of reaction substrate, low costs and easy availability of the catalyst, high product yield and the like, and the technical scheme is verysuitable for industrial mass production. The formulas are shown in the description.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing 2-carbonylthienopyridine compounds. Background technique [0002] 2-Carbonylthienopyridine compounds have important application value in medicinal chemistry and organic synthetic chemistry. For example, thiophene[2,3-b]pyridine compounds can be used as an anti-atherosclerotic agent with high-efficiency bactericidal effect; as a novel multidrug resistance (MDR) regulator, it is important for cancer chemotherapy. value. At the same time, some drug molecules containing thiophene[2,3-b]pyridine can also be used as inhibitors of hepatitis C virus to effectively fight against HCV virus. Other biological activities include anticancer activity, binding to dopamine D2 receptor, acting as IκB kinase-β inhibitor, etc. [1] . Therefore, the efficient and diversified synthesis of 2-carbonylthienopyridine compounds has very important scientific significance and res...

Claims

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Application Information

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IPC IPC(8): C07D495/04
CPCC07D495/04
Inventor 李亦彪罗湘林
Owner WUYI UNIV
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