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Preparation method of vilazodone intermediate

A technology for vilazodone and intermediates, which is applied in the field of preparation of vilazodone intermediates, can solve the problems of unfavorable large-scale industrial production, difficulties in separation and purification, and low synthesis yield, and achieve the advantages of industrial production and raw materials. Inexpensive and easy to obtain, high synthesis efficiency

Inactive Publication Date: 2012-10-17
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] The technical problem to be solved by the present invention is that the synthesis method of 5-nitrobenzofuran-2-carboxylate in the prior art has high cost, low synthesis yield, difficult separation and purification, and is unfavorable for large-scale industrial production. The present invention provides A new method for preparing 5-nitrobenzofuran-2-carboxylate, the method is cheap and easy to obtain raw materials, mild reaction conditions, easy operation, high synthesis efficiency, and is conducive to industrial production

Method used

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  • Preparation method of vilazodone intermediate
  • Preparation method of vilazodone intermediate
  • Preparation method of vilazodone intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Preparation of Compound III (Compound IIa is the compound in which X is Cl in Compound II)

[0033]

[0034] Add 18.7g (0.10mol) of 2-hydroxy-5-nitrobenzyl chloride and 18.3g (0.11mol) of triethyl phosphite into the reaction flask, stir and raise the temperature to 100°C, keep it warm for 3.5 hours, and cool it down for use.

Embodiment 2

[0036] Preparation of compound I (compound IVa is the compound in which R is ethyl in compound IV)

[0037]

[0038] Dissolve the compound III obtained in Example 1 in 175ml of anhydrous DMF, control the temperature in an ice bath at 0-5°C, add 27.2g (0.4mol) of sodium ethoxide, and drop 15.0g (0.11mol) of oxalyl chloride at 5°C After the addition of monoethyl ester was completed and reacted at room temperature for 5 hours, 200ml of ice water was added, extracted with ethyl acetate, the organic phase was washed twice with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the residue was recrystallized with methanol to obtain White solid 14.5g, melting point: 140-141°C, total yield 62%.

[0039] Its structural identification data are as follows:

[0040] 1 HNMR (300MHz, CDCl 3 ), δ (ppm): 8.65 (1H, d), 8.37 (1H, dd), 7.73 (1H, d), 7.64 (1H, s), 4.48 (2H, q), 1.46 (3H, t).

Embodiment 3

[0042] Preparation of compound III (compound IIb is the compound in which X is Br in compound II)

[0043]

[0044] Add 23.1 g (0.10 mol) of 2-hydroxy-5-nitrobenzyl bromide and 18.3 g (0.11 mol) of triethyl phosphite into the reaction flask, stir and raise the temperature to 100° C., keep the temperature for 3.5 hours, and cool for later use.

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Abstract

The invention discloses a preparation method of a vilazodone intermediate 5-nitrobenzofuran-2-formate, which comprises the following steps: (1) heating a compound II and triethyl phosphite to react, thereby obtaining a compound III; and (2) reacting the compound III with a compound IV in an organic solvent under the action of alkali, thereby obtaining a compound I, wherein X is a halogen or hydroxyl group, and R is a C1-C6 straight-chain alkyl group or alkyl group with branched chains. The invention is simple to operate, has the advantages of mild reaction conditions, stable quality and simple after-treatment, and is suitable for industrial production. Step (1) Step (2).

Description

technical field [0001] The invention relates to a preparation method of an intermediate 5-nitrobenzofuran-2-carboxylate of vilazodone. Background technique [0002] Depression is a common affective disorder mental illness. Its clinical manifestations are depression, pessimism, sleep disturbance, etc. In severe cases, suicidal impulses often appear. It is one of the most disabling diseases in the world. According to WTO statistics, the prevalence of various types of depression has accounted for 3% to 5% of the global population. By 2020, depression may become the second largest disease after heart disease. There are many treatment methods for depression. In the past, psychotherapy was mainly given. In the past 20 years, with the progress of research on the etiology of depression, the leading position of drug treatment has been gradually established. [0003] Vilazodone (Formula A) is a novel antidepressant with a dual mechanism of action, namely a selective serotonin (5-HT) ...

Claims

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Application Information

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IPC IPC(8): C07D307/85
Inventor 陈国华李楠江传亮刘晓君
Owner CHINA PHARM UNIV
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