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Synthesis method of drug intermediate-aryl sulfenyl compound

A synthesis method and compound technology are applied in the synthesis of pharmaceutical intermediates aryl sulfinyl compounds, the synthesis of sulfinyl compounds, and the fields of organic synthesis, which can solve the problems that the reaction yield needs to be further improved, and achieve good application prospects and The effect of industrial production potential

Inactive Publication Date: 2015-12-02
方美兰
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Yet, the reaction yield of these methods of prior art still needs to be further improved

Method used

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  • Synthesis method of drug intermediate-aryl sulfenyl compound
  • Synthesis method of drug intermediate-aryl sulfenyl compound
  • Synthesis method of drug intermediate-aryl sulfenyl compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029]

[0030] Under a nitrogen atmosphere, add 100mmol of the above formula (I) compound, 150mmol of the above formula (II) compound, 8mmol Catalyst (a mixture of 6.65mmol acetylferrocene and 1.35mmol nickel tetracarbonyl), 10mmol additive N-butyl-N-methylpyrrolidine bis(trifluoromethanesulfonyl)imide salt and 40mmol base triisopropyl Alcohol amine, then stirred and reacted at 40°C for 10 hours. After the reaction, a mixture of deionized water and ethyl acetate with a volume ratio of 1:2 was added to the reaction system, fully shaken, and the organic phase was separated, and the water phase was used Extract with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, filter, distill under reduced pressure, and separate the residue through a silica gel column to obtain the compound of formula (III) with a yield of 97.4%.

[0031] 1 HNMR (CDCl 3 ,400MHz): δ7.52(d,J=8.1Hz,2H),7.24(d,J=8.1Hz,2H),7.19(d,J=8.4Hz,2H),7.12(d,J=8.4Hz , 2H), 4.88 (d, J = 11...

Embodiment 2

[0033]

[0034] Under a nitrogen atmosphere, add 100 mmol of the above formula (I) compound, 175 mmol of the above formula (II) compound, 10.5 mmol catalyst (a mixture of 7.5 mmol acetylferrocene and 3 mmol nickel tetracarbonyl), 15 mmol additive N-butyl-N-methylpyrrolidine bis(trifluoromethanesulfonyl) imide salt and 50 mmol base triisopropyl Alcohol amine, then stirred and reacted at 50°C for 8 hours. After the reaction, a mixture of deionized water and ethyl acetate with a volume ratio of 1:2 was added to the reaction system, fully shaken, and the organic phase was separated, and the water phase was used Extract with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, filter, distill under reduced pressure, and separate the residue through a silica gel column to obtain the compound of formula (III) with a yield of 97.6%.

[0035] 1 HNMR (CDCl 3,400MHz): δ7.66(d,J=7.8Hz,2H),7.52(d,J=7.9Hz,1H),7.37–7.14(m,5H),5.11(d,J=12.2Hz,1H) , 4.72 (d, J=12...

Embodiment 3

[0037]

[0038] Under a nitrogen atmosphere, add 100mmol of the above formula (I) compound, 200mmol of the above formula (II) compound, 15mmol Catalyst (a mixture of 11.5mmol acetylferrocene and 3.5mmol nickel tetracarbonyl), 20mmol additive N-butyl-N-methylpyrrolidine bis(trifluoromethanesulfonyl)imide salt and 60mmol base triisopropyl Alcohol amine, then stirred and reacted at 60°C for 6 hours. After the reaction, a mixture of deionized water and ethyl acetate with a volume ratio of 1:2 was added to the reaction system, fully shaken, the organic phase was separated, and the water phase was used Extract with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, filter, distill under reduced pressure, and separate the residue through a silica gel column to obtain the compound of formula (III) with a yield of 97.1%.

[0039] 1 HNMR (CDCl 3 ,400MHz):δ7.55(d,J=7.9Hz,2H),7.26–7.18(m,7H),4.95(d,J=11.4Hz,1H),4.48(d,J=11.4Hz,1H) ,2.34(s,3H).

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Abstract

The invention relates to a synthesis method of an aryl sulfenyl compound shown as a formula (III). The synthesis method includes: under a nitrogen atmosphere, in organic solvent and in the presence of catalyst, additive and alkali, stirring a compound shown as (I) and a compound shown as (II) at 40-60 DEG C for reaction for 6-10h; after reaction is finished, adding mixed liquid of deionized water and ethyl acetate according to a volume ratio of 1:2 into a reaction system; sufficiently oscillating to separate organic phase, using water to extract ethyl acetate, and merging the organic phase; using anhydrous sodium sulfide to dry, filtering, depressurizing for distillation, and enabling residue to pass a silica gel column for separation to obtain the compound shown as the formula (III), wherein R1-R2 are chosen from H, C1-C6 alkyl or halogens respectively and independently. By the synthesis method, a target product can be obtained with high yield under comprehensive synergistic promoting action of the catalyst, the additive and the alkali by properly selecting matrixes; the synthesis method has good application prospect and industrialized production potential in the technical field of drug intermediate synthesis.

Description

technical field [0001] The invention relates to a method for synthesizing sulfinyl compounds, more particularly to a method for synthesizing aryl sulfinyl compounds as pharmaceutical intermediates, and belongs to the field of organic synthesis, especially the synthesis of pharmaceutical intermediates. Background technique [0002] In the field of organic chemistry, especially medicinal chemistry, sulfonyl compounds or sulfinyl compounds are an important class of pharmaceutical intermediates, which endow compounds with outstanding reactivity and drug Activity, currently a variety of marketed drugs contain sulfonyl or sulfinyl groups, such as various sulfonamide drugs. [0003] It is precisely because of the important medical use of sulfonyl compounds or sulfinyl compounds that people have conducted a lot of in-depth research on their synthesis and achieved many results, such as: [0004] S.Chandrasekhar et al. ("Hydroxy-assistedcatalyst-freeMichaeladdition-dehydroxylationofB...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C313/04
Inventor 方美兰
Owner 方美兰