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A kind of synthetic method of alkyne-substituted quinolinone compound of pharmaceutical intermediate

A synthesis method and technology of quinolinones, applied in the synthesis of quinolinones and the synthesis of alkynyl-substituted quinolinones, can solve problems such as few reports, and achieve good application prospects and industrial production value Effect

Active Publication Date: 2017-10-03
兰州迪瑞生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] However, there are few reports on the selective alkynylation of quinolinones in the prior art

Method used

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  • A kind of synthetic method of alkyne-substituted quinolinone compound of pharmaceutical intermediate
  • A kind of synthetic method of alkyne-substituted quinolinone compound of pharmaceutical intermediate
  • A kind of synthetic method of alkyne-substituted quinolinone compound of pharmaceutical intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034]

[0035] In an appropriate amount of organic solvent (being the mixture of NMP and PEG-200 whose volume ratio is 5:1) in the reactor at room temperature, add 100mmol of the compound of formula (I) above and 100mmol of the compound of formula (II) above, and stir and mix for 10 minutes, then 3 mmol of catalyst (to be 2.4 mmol [RhCp*Cl 2 ] 2 with 0.6mmolAgBF 4 mixture) and 8mmol of auxiliary cucurbit[7]uril, heated to 50°C and kept stirring for 8 hours; after the reaction was completed, the reaction mixture was filtered, deionized water was added to the filtrate and fully shaken, and extracted with dichloromethane for 2-3 Second, the organic phases were combined, distilled under reduced pressure, and the residue was subjected to silica gel column chromatography to obtain the compound of formula (III) (wherein Bn is benzyl) in a yield of 96.5%.

[0036] 1 H NMR (CDCl 3 ,400MHz):δ7.66(d,J=9.3Hz,1H),7.46(d,J=7.9Hz,1H),7.41-7.27(m,3H),7.18(d,J=9.3Hz,1H) , 7.09 (ddd, J...

Embodiment 2

[0038]

[0039] In an appropriate amount of organic solvent (being a mixture of NMP and PEG-200 with a volume ratio of 5:1) in the reactor at room temperature, add 100mmol of the compound of the above formula (I) and 120mmol of the compound of the above formula (II), and stir and mix for 12 minutes, then 4 mmol of catalyst (to be 3.2 mmol [RhCp*Cl 2 ] 2 with 0.8mmolAgBF 4 mixture) and 12mmol of auxiliary cucurbit[7]uril, heated to 55°C and kept stirring for 7 hours; after the reaction was completed, the reaction mixture was filtered, deionized water was added to the filtrate and fully shaken, and extracted with dichloromethane for 2-3 Second, the organic phases were combined, distilled under reduced pressure, and the residue was subjected to silica gel column chromatography to isolate the compound of formula (III) (wherein Bn was benzyl) with a yield of 96.3%.

[0040] 1 H NMR (CDCl 3 ,400MHz):δ7.44(d,J=7.8Hz,1H),7.34-7.23(m,3H),7.19-7.07(m,2H),7.02(dd,J=7.8,1.8Hz,2H), 6...

Embodiment 3

[0042]

[0043] In an appropriate amount of organic solvent (being a mixture of NMP and PEG-200 with a volume ratio of 5:1) in the reactor at room temperature, add 100mmol of the compound of formula (I) above and 150mmol of the compound of formula (II) above, and stir and mix for 15 minutes, then add 5 mmol of catalyst (to be 4 mmol [RhCp*Cl 2 ] 2 with 1mmolAgBF 4 mixture) and 10mmol of auxiliary cucurbit[7]uril, heated to 60°C and kept stirring for 6 hours; after the reaction was completed, the reaction mixture was filtered, deionized water was added to the filtrate and fully shaken, and extracted with dichloromethane for 2-3 For the second time, the organic phases were combined, distilled under reduced pressure, and the residue was subjected to silica gel column chromatography to isolate the compound of the above formula (III) with a yield of 96.2%.

[0044] 1 H NMR (CDCl 3 ,400MHz):δ7.57-7.43(m,2H),7.29(d,J=7.7Hz,1H),7.24(dd,J=8.3,1.5Hz,1H),6.13(d,J=7.7Hz, 1H), 3.72...

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Abstract

The present invention relates to providing a method for synthesizing alkynyl substituted quinolinone compounds shown in formula (III), said method comprising: adding a compound of formula (I) and a compound of formula ( II) compound, and stir and mix for 10-15 minutes, then add catalyst and additive, heat up to 50-60°C and keep stirring for 6-8 hours; after the reaction is completed, filter the reaction mixture, add deionized water to the filtrate to fully Oscillate, extract 2-3 times with dichloromethane, combine organic phase, underpressure distillation, residue crosses silica gel column chromatography, separates and obtains formula (III) compound, wherein, R1 is selected from C1-C6 alkyl or benzyl, R2 selected from H, C1-C6 alkoxy, nitro or halogen. The method has a unique synergistic effect through the proper selection and combination of catalysts, auxiliary agents and organic solvents, and can obtain the target product with high yield, and has good application prospects and industrial production value in the field of organic synthesis.

Description

technical field [0001] The invention relates to a method for synthesizing quinolinone compounds, more particularly to a method for synthesizing alkynyl-substituted quinolinone compounds, and belongs to the field of synthesis of pharmaceutical intermediates. Background technique [0002] In organic chemistry and medicinal chemistry, quinolinones are important building blocks for building natural or synthetic drugs, lead compounds, functional materials, etc. For example, C5-alkynyl quinolinones have been reported as intermediates for the preparation of biologically active drugs , [0003] It is precisely because of the important role and application potential of quinolinone compounds that the development of selective alkynylation of quinolinone compounds has increasingly become one of the key issues in the field of synthesis. [0004] In addition, because alkynyl is an unsaturated group, it has good reactivity and can further undergo various reactions, so it can be used as a ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/10
Inventor 海青宏刘洁丽
Owner 兰州迪瑞生物科技有限公司
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