Synthesis method of 2-amino-4-fluoropyridine

A synthetic method, fluoropyridine technology, applied in the direction of organic chemistry, etc., can solve the problems of complex operation, low yield, serious pollution, etc., and achieve the effect of simple operation process and cheap and easy-to-obtain reagents

Inactive Publication Date: 2018-03-06
SHANGHAI LINKCHEM TECH CO LTD
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Problems solved by technology

[0003] Although the synthesis of 4-fluoro-2-aminopyridine has been reported, most reports are not to use 2-aminopyridine as raw material to synthesize 4-fluoro-2-aminopyridine, and their synthetic routes are long, complicated to operate, seriously polluted, High cost and low yield, so not suitable for industrial production

Method used

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  • Synthesis method of 2-amino-4-fluoropyridine
  • Synthesis method of 2-amino-4-fluoropyridine
  • Synthesis method of 2-amino-4-fluoropyridine

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Embodiment

[0026] 1) Preparation of 2-aminopyridine N-oxide

[0027] Acetic acid (220mL) and acetic anhydride (110mL) were added into a 1L four-necked flask, and raw material diaminopyridine (94.2g, 1.0mol) and hydrogen peroxide (200ml, 1.9mol) with a mass concentration of 30% were added successively under stirring at room temperature, and the Stir at 75°C for 3h, add acetic anhydride (50ml) and 30% hydrogen peroxide (90ml, 0.9mol), and continue the reaction for 3h. After the reaction, the solvent was distilled off under reduced pressure, and the residue was cooled to room temperature, and adjusted to pH = 7-8 with saturated sodium carbonate solution. Extract with chloroform (100mL×3), and recover the solvent in the organic phase under reduced pressure at low temperature to obtain an orange-red liquid containing compound a, which is directly used in the next reaction without purification. The reaction formula is as follows:

[0028]

[0029] 2) Preparation of 2-amino-4-nitropyridine...

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Abstract

The invention discloses a synthesis method of 2-amino-4-fluoropyridine. The synthesis method comprises the following synthesis steps: 1, taking diaminopyridine as the raw material, carrying out oxidation reaction to prepare 2-aminopyridine N-oxide a; 2, subjecting the compound a to nitration reaction with mixed acid to obtain 2-amino-4-nitropyridine N-oxide b; 3, carrying out acylation reaction onthe compound b and an acylation reagent to obtain 2-acetamino-4-nitropyridine N-oxide c; 4, carrying out reduction reaction on the compound c to obtain 2-acetamino-4-aminopyridine d; 5, carrying outdiazo-reaction on the compound d and HBF4 to obtain diazonium fluoroborate e; and 6, carrying out Balz-Schiemann reaction on the compound e to introduce fluorine atoms and conducting hydrolysis deacetylation to obtain 2-amino 4-fluoropyridine. The method provided by the invention solves the problems of long synthesis route, complicated operation, serious pollution, high cost, low yield and the like in existing synthesis methods.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a synthesis method of 2-amino-4-fluoropyridine, which plays an important role in the field of new drug research. Background technique [0002] Aminopyridine compounds are widely used in the fields of modern pesticides and medicines, and are important intermediates. 4-Fluoro-2-aminopyridine is an important intermediate for preparing various inhibitors such as tyrosine kinase inhibitors, PI3K inhibitors and aldosterone synthase inhibitors, and has broad application prospects. [0003] Although the synthesis of 4-fluoro-2-aminopyridine has been reported, most reports are not to use 2-aminopyridine as raw material to synthesize 4-fluoro-2-aminopyridine, and their synthetic routes are long, complicated to operate, seriously polluted, The cost is high and the yield is low, so it is not suitable for industrial production. Contents of the invention [0004] In view of the above-menti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/73
CPCC07D213/73
Inventor 陆茜
Owner SHANGHAI LINKCHEM TECH CO LTD
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