Synthesis method of (2-fluoro-6-(trifluoromethyl) pyridine-3-yl) methanol

A technology of trifluoromethyl and synthesis method is applied in the synthesis field of (2-fluoro-6-(trifluoromethyl)pyridin-3-yl)methanol and achieves the effects of reasonable design, easy control and high yield

Active Publication Date: 2020-11-10
阿里生物新材料(常州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Benefits of technology

In this patented process, we have developed an efficient way to make certain chemical substances that can be used to treat diseases or improve their symptoms. These methods are designed based on specific molecular structures found within these drugs (called targets). By combining different types of reagents together at once, it becomes possible to create new products without having complex steps like chemistry or biology techniques.

Problems solved by technology

This patented describes different methods for making certain chemicals called pyridine nucleotides or their analogues (PNA). However, current methods involve expensive starting material and complicated operations which make them difficult to produce at an industrially viable level.

Method used

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  • Synthesis method of (2-fluoro-6-(trifluoromethyl) pyridine-3-yl) methanol

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[0018] A method for synthesizing (2-fluoro-6-(trifluoromethyl)pyridin-3-yl)methanol, comprising the following steps:

[0019] (1) The mass ratio of compound A and diisopropylamine is 5:3~5, the solid-liquid g / mL ratio of compound A and tetrahydrofuran is 1:14, and the volume ratio of tetrahydrofuran and n-butyllithium in hexane is 5:1, take raw materials, then put diisopropylamine and tetrahydrofuran into the reactor, stir, protect with nitrogen, cool down to -80~-75℃, add n-butyllithium hexane solution, stir for 1~1.5h , then add Compound A, continue to stir for 2-3 hours, pass in carbon dioxide, heat up to 30-35°C, and react for 1-2 hours to obtain Compound B;

[0020] (2) According to the solid-liquid g / mL ratio of compound B and tetrahydrofuran as 1:20, and the volume ratio of borane dimethyl sulfide to tetrahydrofuran as 1:13-15, take raw materials, and then mix compound B and tetrahydrofuran evenly , protected by nitrogen, lower the temperature at -2~0°C, add borane dim...

Embodiment 1

[0022]

[0023] Preparation of Compound B:

[0024] Put 5g of diisopropylamine and 70mL of tetrahydrofuran into the reactor, stir evenly, under nitrogen protection, cool down to -80°C, add 14mL of n-butyllithium hexane solution (2.5M), stir for 1h, then add 5g of compound A, Continue to stir for 2 hours, replace with carbon dioxide, raise the temperature to 30°C, react for 2 hours, and detect by TLC. After the reaction of the raw materials is complete, add water (50mL) dropwise to quench the reaction, add 5g of potassium carbonate to the reaction solution, and extract impurities with ethyl acetate (50mL *2), the aqueous phase was adjusted to pH 2 with 4M hydrochloric acid, extracted with ethyl acetate (50mL*2), and the organic phase was concentrated to obtain 4.8g of a colorless and transparent oily substance, namely Compound B, with a yield of 75.8% and a purity of 96.8%.

[0025]

[0026] Preparation of Compound C, i.e. (2-fluoro-6-(trifluoromethyl)pyridin-3-yl)methan...

Embodiment 2

[0031]

[0032] Preparation of compound B:

[0033] Put 4g of diisopropylamine and 70mL of tetrahydrofuran into the reactor, stir evenly, under nitrogen protection, cool down to -75°C, add 14mL of n-butyllithium hexane solution (2.5M), stir for 1.5h, then add 5g of compound A , continue to stir for 3 hours, pass in carbon dioxide, heat up to 35 ° C, react for 2 hours, TLC detection, the reaction of the raw materials is complete, drop water (50 mL) to quench the reaction, add 5 g of potassium carbonate to the reaction solution, and extract impurities with ethyl acetate (50 mL* 2), the aqueous phase was adjusted to pH 2 with 4M hydrochloric acid, extracted with ethyl acetate (50mL*2), and the organic phase was concentrated to obtain 5g of a colorless and transparent oil, namely compound B, with a yield of 78.9% and a purity of 98.2% .

[0034]

[0035] Preparation of compound C, i.e. (2-fluoro-6-(trifluoromethyl)pyridin-3-yl)methanol:

[0036] Mix 3g of compound B and 60...

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Abstract

The invention belongs to the technical field of medical intermediates, and particularly relates to a synthesis method of (2-fluorin- 6-(trifluoromethyl) pyridine-3-yl) methanol. According to the invention, a compound A is used as an initial raw material and reacts with diisopropylamine under the catalysis of n-butyllithium to obtain a compound B, and the compound B reacts with borane dimethyl sulfide to obtain the (2-fluorine-6-(trifluoromethyl) pyridine-3-yl) methanol, so that the synthesis method of the (2-fluorine-6 (trifluoromethyl) pyridine-3-yl) methanol is provided for the first time. The synthetic method provides a synthetic route for the synthesis of the (2-fluorine-6 (trifluoromethyl) pyridine-3-yl) methanol, and is short in route, reasonable in design, simple to operate and easyto control.

Description

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Claims

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Application Information

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Owner 阿里生物新材料(常州)有限公司
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