2-methoxy-5-(pyridine-2-yl)pyridine synthesis method

A methoxypyridine, methoxyl technology, applied in the field of medicinal chemistry, can solve the problem of high cost, achieve the effects of low cost, convenient large-scale production and simple operation

Inactive Publication Date: 2016-08-31
BEIJING VENTUREPHARM BIOTECH
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Problems solved by technology

[0003] Patent CN104649963A discloses the synthesis method of perampanel intermediate 2-methoxy-5-(pyridin-2-yl)pyridine, using 5-bromo-2-methoxypyridine and bispinacol diboron in palladium catalysis Lower coupling, this method has adopted palladium as catalyst, the cost is higher

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  • 2-methoxy-5-(pyridine-2-yl)pyridine synthesis method

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Embodiment

[0020] Add 1.57 gK2CO3 and 6.25 ml DMF to a 100ml three-necked flask equipped with a thermometer, a constant pressure dropping funnel, and magnetic stirring. Stir, add 1.41 ml 5-bromo-2-methoxypyridine slowly, and the addition is complete. Slowly add 2.07 g of nadiboron, stirring, and react for 2 hours. Add 1.7 g of 2-chloropyridine and stir to react for 3 hours, dilute with water, stir for 20 min, and separate; the aqueous phase is extracted with ethyl acetate, the organic phases are combined, washed twice with saturated brine, and concentrated under reduced pressure to obtain the middle of perampanel Body yellow oil, purity 83%, yield 85%.

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Abstract

The invention belongs to the field of medicinal chemistry and relates to a preparation technology of 2-methoxy-5-(pyridine-2-yl)pyridine as a perampanel intermediate. The preparation technology comprises that 5-bromo-2-methoxypyridine and bis(pinacolato)diboron undergo a reaction to produce 2-methoxypyridine-5-boronic acid pinacol ester and the 2-methoxypyridine-5-boronic acid pinacol ester and 2-halogenated pyridine undergo a reaction to produce 2-methoxy-5-(pyridine-2-yl)pyridine as a perampanel intermediate. The synthesis method solves the problem of a high catalyst cost, has the advantages of simple processes and low cost and is convenient for large scale production.

Description

Technical field [0001] The invention belongs to the field of medicinal chemistry, and mainly relates to a preparation process of 2-methoxy-5-(pyridin-2-yl)pyridine, an intermediate of perampanel. Background technique [0002] Perampanel, English name Perampanel, chemical name 3-(2-Cyanopheny1)-1-pheny1-5-(2-pyridy1)-1,2-dihydropyridin-2-one, is a product developed by Eisai Pharmaceuticals, USA This AMPA receptor antagonist is used as an adjuvant therapy for partial seizures in patients with epilepsy over 12 years old, regardless of whether the patient is accompanied by secondary general seizures. It was launched in the United States in October 2012 under the trade name Fycompa. [0003] Patent CN104649963A discloses the synthesis method of perampanel intermediate 2-methoxy-5-(pyridin-2-yl)pyridine, which uses 5-bromo-2-methoxypyridine and bispinacol diboron in palladium catalysis Under coupling, this method uses palladium as a catalyst, and the cost is relatively high. Summary o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/64
CPCC07D213/64
Inventor 陈孟南赵国磊
Owner BEIJING VENTUREPHARM BIOTECH
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