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Synthesis method of 3-cyclic ether methyl trifluoro-potassium borate

A technology of potassium methyl trifluoroborate and its synthesis method, which is applied in the fields of compounds containing group 3/13 elements of the periodic table, chemical instruments and methods, organic chemistry, etc., and can solve environmental heavy metal pollution, increased production costs, and difficult raw materials To achieve cheap price, simple post-processing, good maneuverability and repeatability

Active Publication Date: 2014-07-02
SUNDIA MEDITECH COMPANY LTD
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AI Technical Summary

Problems solved by technology

[0016] For the synthesis of 3-cyclic ether methyl pinacol borate, if a similar method is used, the corresponding raw materials are not easy to obtain, the price is expensive or multi-step synthesis is required To obtain, such as tetrahydropyran-3-carboxaldehyde sigma price 25mg 86 US dollars, 3-methyltetrahydropyran and 3-methylenetetrahydropyran both need two steps to be synthesized (Formula 5); The reaction using a catalyst will not only cause heavy metal pollution to the environment, but also increase production costs

Method used

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  • Synthesis method of 3-cyclic ether methyl trifluoro-potassium borate
  • Synthesis method of 3-cyclic ether methyl trifluoro-potassium borate
  • Synthesis method of 3-cyclic ether methyl trifluoro-potassium borate

Examples

Experimental program
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Embodiment 1

[0029] 1) 3-tetrahydrofuryl pinacol borate

[0030] In a dry 1000mL three-necked flask, add 25 g of 2,3-dihydrofuran and 120 mL of anhydrous tetrahydrofuran, cool the reaction solution to 0°C, and slowly add 360 mL of 1M borane / tetrahydrofuran solution dropwise into the reaction solution. 44 g of pinacol was dissolved in 100 mL of tetrahydrofuran, and slowly added dropwise to the reaction solution. The reaction solution was stirred overnight at room temperature. Water was slowly added dropwise to the reaction solution, extracted with ethyl acetate, the organic phase was concentrated and then purified by flash column chromatography to obtain 29 g of 3-tetrahydrofuryl pinacol borate with a yield of 41%. 1 H-NMR (300 MHz, CDCl 3 ): δ3.93-3.96 (m, 1H), 3.75-3.81 (m, 1H), 3.56-3.71 (m, 2H), 1.97-2.02 (m, 1H), 1.76-1.87 (m, 1H), 1.54 -1.60 (m, 1H), 1.25 (s, 12H).

[0031] ) 3-tetrahydrofuranmethyl pinacol borate

[0032] In a dry 500mL three-necked flask, add 29g of 3-tetra...

Embodiment 2

[0036] 1) 3-tetrahydropyranyl pinacol borate

[0037] In a dry 1000mL three-necked flask, add 25 g of 3,4-dihydropyran and 120 mL of anhydrous tetrahydrofuran, cool the reaction solution to 0°C, and slowly add 300 mL of 1M borane / tetrahydrofuran solution dropwise into the reaction solution . 35 g of pinacol was dissolved in 100 mL of tetrahydrofuran, and slowly added dropwise to the reaction solution. The reaction solution was stirred overnight at room temperature. Water was slowly added dropwise to the reaction solution, extracted with ethyl acetate, the organic phase was concentrated and then purified by flash column chromatography to obtain 28 g of 3-tetrahydropyranyl pinacol borate with a yield of 45%. 1 H-NMR (300 MHz, CDCl 3 ): δ3.78-3.89 (m, 2H), 3.40-3.51 (m, 2H), 1.79-1.82 (m, 1H), 1.48-1.57 (m, 3H), 1.29-1.32 (m, 1H), 1.23 (s, 12H).

[0038] ) 3-Tetrahydropyranylmethyl pinacol borate

[0039] Preparation of lithium diisopropylamide (LDA): In a dry 500 mL thre...

Embodiment 3

[0044] 1) 2-(4-chlorophenyl)-4-(3-tetrahydrofurylmethyl)thieno[2,3-d]pyrazine-7-carboxamide

[0045] In a dry 250 mL three-necked flask, 4-chloro-2-(4-c chlorophenyl)-thieno[2,3-d]pyrazine-7-carboxamide (10.0 g) was added under nitrogen protection, Anhydrous tetrahydrofuran (100 mL) and 1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (1.13g), then potassium 3-tetrahydrofuranmethyl trifluoroborate (6.53g), The reaction mixture was stirred overnight at 60 °C. After cooling to room temperature, saturated aqueous ammonium chloride solution was added, the layers were separated, and the aqueous layer was extracted with ethyl acetate. After combining the organic layers, they were washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to remove the solvent to obtain a crude product. The crude product was purified by column chromatography on silica gel (petroleum ether / ethyl acetate volume ratio=5 / 1) to obtain 7.04 g of 2-(4-chlorophenyl)-4-(3-...

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Abstract

The invention relates to 3-cyclic ether methyl trifluoro-potassium borate, in particular relates to a synthesis method of 3-cyclic ether methyl trifluoro-potassium borate, mainly solving the technical problems of the existing preparation method that the catalyst is expensive, the reaction condition is severe, the synthesis process is long and the like. According to the technical scheme, the synthesis method comprises the following steps: performing an addition reaction on 2-cyclic ether olefin taken as a raw material and borane; quenching with pinacol so as to obtain 3-cyclic ether-based pinacol boric acid ester; removing protons from the 3-cyclic ether-based pinacol acid ester by using a strong alkali and reacting with chlorobromomethane so as to obtain 3-cyclic ether methyl pinacol boric acid ester; and finally, performing a reaction on the 3-cyclic ether methyl pinacol boric acid ester and potassium bifluoride so as to obtain the 3-cyclic ether methyl trifluoro-potassium borate. The 3-cyclic ether methyl trifluoro-potassium borate is an important medicinal compound structure-modified micromolecule in the research field of a novel medicine.

Description

technical field [0001] The invention relates to potassium 3-cycloethermethyl trifluoroborate, in particular to a synthesis method of potassium 3-cycloethermethyl trifluoroborate. This type of compound is an important structure-modifying small molecule of a pharmaceutical compound in the field of new drug research. Background technique [0002] Boronic acid compounds and their derivatives are a class of compounds that have attracted widespread attention in the field of organic synthesis. They have the characteristics of stable properties, high reactivity, and environmental protection. Such compounds are usually used as intermediates in transition metal-catalyzed reactions as electrophilic centers to construct C-C bonds. Compared with coupling reactions involving Grignard reagents, zinc reagents, and lithium reagents, this type of reaction has better functional group tolerance . In recent years, with the development of catalysts for the coupling reaction of borate compounds w...

Claims

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Application Information

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IPC IPC(8): C07F5/04C07D495/04
Inventor 侯海荣曹丹
Owner SUNDIA MEDITECH COMPANY LTD
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