CN110256382A - A kind of synthetic method of 2- (5- methyl benzofuran -2- base) benzonitrile - Google Patents

A kind of synthetic method of 2- (5- methyl benzofuran -2- base) benzonitrile Download PDF

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Publication number
CN110256382A
CN110256382A CN201910490310.9A CN201910490310A CN110256382A CN 110256382 A CN110256382 A CN 110256382A CN 201910490310 A CN201910490310 A CN 201910490310A CN 110256382 A CN110256382 A CN 110256382A
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CN
China
Prior art keywords
benzonitrile
base
compound
methyl benzofuran
synthetic method
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN201910490310.9A
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Chinese (zh)
Inventor
毛晶
王密
杨云龙
刘爽
汪永生
陈冬枝
庞洲
张宏伟
于凌波
马汝建
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Wuxi Apptec Wuhan Co Ltd
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Wuxi Apptec Wuhan Co Ltd
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Priority to CN201910490310.9A priority Critical patent/CN110256382A/en
Publication of CN110256382A publication Critical patent/CN110256382A/en
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The present invention relates to a kind of synthetic methods of 2- (5- methyl benzofuran -2- base) benzonitrile, the technical issues of mainly solution currently without suitable Industrialized synthesis method.The present invention is 1 step, and by compound 1 and compound 2, reaction obtains final compound 3 under the action of sodium ethoxide in solvent n,N dimethylformamide and ethyl alcohol.Reaction equation is as follows:

Description

A kind of synthetic method of 2- (5- methyl benzofuran -2- base) benzonitrile
Technical field
The present invention relates to the synthetic methods of compound 2- (5- methyl benzofuran -2- base) benzonitrile.
Background technique
Compound 2- (5- methyl benzofuran -2- base) benzonitrile (143381-79-7) and relevant derivative are in drug Have in chemistry and organic synthesis and is widely applied.2- (5- methyl benzofuran -2- base) benzonitrile synthetic method rarely has text at present Offer report.It is easy to operate therefore, it is necessary to develop a raw material to be easy to get, react easily controllable, overall yield is suitble to, and is suitble to industry The synthetic method that metaplasia produces.
Summary of the invention
It is easy to operate the purpose of the present invention is developing one kind to be easy to get with raw material, react easily controllable, the higher 2- of yield The synthetic method of (5- methyl benzofuran -2- base) benzonitrile.Mainly solve the skill currently without suitable Industrialized synthesis method Art problem.
Technical solution of the present invention: a kind of synthetic method of 2- (5- methyl benzofuran -2- base) benzonitrile, the present invention are 1 step is reacted under the action of sodium ethoxide in solvent n,N dimethylformamide and ethyl alcohol by compound 1 and compound 2 and is obtained most Whole compound 3, reaction equation is as follows:
90 DEG C of reaction temperature 3 hours of reaction.
The Chinese paraphrase that the present invention abridges: DMF:N, N-dimethylformamide；EtOH: ethyl alcohol；EtONa: sodium ethoxide.
Beneficial effects of the present invention: reaction process of the present invention design rationally, which employs be easy to get, can large-scale production original Expect 2- cyano benzyl bromine, 2- (5- methyl benzofuran -2- base) benzonitrile is synthesized by 1 step, this method route is short, and yield is reachable 60%, reaction is easy to amplify, easy to operate.
Specific embodiment
Reaction equation of the present invention is as follows:
Embodiment 1:
Compound 2(25.04 g, 184 mmol are dissolved in n,N dimethylformamide (180 mL) and ethyl alcohol (90 mL), Then room temperature sequentially adds sodium ethoxide (10.8 g, 199 mmol) and compound 1 (35 g, 179 mmol), in nitrogen ring It stirs, is then reacted at 90 DEG C 3 hours under border, TLC (petrol ether/ethyl acetate volume ratio=5/1) display has been reacted Finish.Then, concentration removes the ethyl alcohol in solvent.Water (90 mL) is added into mixture, crude product is then obtained by filtration.By crude product It carries out column chromatography for separation (gradient elution: petroleum ether~petrol ether/ethyl acetate volume ratio=100/1 ~ 20/1) and obtains sterling Compound 3(25 g, 107 mmol).Yield 60.3%.
1 DMSO δ= 7.79~7.70 (m, 3H), 7.60~7.54 (m, 3H), 7.30~7.14 (m, 2H), 2.34 (3, 3H)。

Claims (2)

1. a kind of synthetic method of 2- (5- methyl benzofuran -2- base) benzonitrile, it is characterized in that: by compound 1 and compound 2 Reaction obtains final compound 3 under the action of sodium ethoxide in solvent n,N dimethylformamide and ethyl alcohol, and reaction equation is as follows:
。
2. a kind of synthetic method of 2- (5- methyl benzofuran -2- base) benzonitrile according to claim 1, feature It is: 90 DEG C of reaction temperature, reacts 3 hours.
CN201910490310.9A 2019-06-06 2019-06-06 A kind of synthetic method of 2- (5- methyl benzofuran -2- base) benzonitrile Pending CN110256382A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201910490310.9A CN110256382A (en) 2019-06-06 2019-06-06 A kind of synthetic method of 2- (5- methyl benzofuran -2- base) benzonitrile

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201910490310.9A CN110256382A (en) 2019-06-06 2019-06-06 A kind of synthetic method of 2- (5- methyl benzofuran -2- base) benzonitrile

Publications (1)

Publication Number Publication Date
CN110256382A true CN110256382A (en) 2019-09-20

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Country Status (1)

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992016552A1 (en) * 1991-03-25 1992-10-01 Glaxo Group Limited 1-imidazolgemethyl benzofuran derivatives as inhibitors of angiotensin ii activity
EP0514192A1 (en) * 1991-05-16 1992-11-19 Glaxo Group Limited Antihypertensive benzofuran derivatives, substituted by varied N-pyrimidinyl- or N-imidazolyl-methyl groups
US5252593A (en) * 1991-05-16 1993-10-12 Glaxo Group Limited Pyrazole containing benzofuran derivatives and pharmaceutical compositions
US5332831A (en) * 1991-05-16 1994-07-26 Glaxo Group Limited Benzofuran derivatives
US5374721A (en) * 1992-10-14 1994-12-20 Merck & Co., Inc. Benzo-fused lactams promote release of growth hormone
WO2000078726A1 (en) * 1999-06-18 2000-12-28 Eli Lilly And Company Imidazoline derivatives for the treatment of diabetes, especially type ii diabetes
US20020128290A1 (en) * 1995-05-19 2002-09-12 Etsuo Ohshima Derivatives of benzofuran or benzodioxole

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992016552A1 (en) * 1991-03-25 1992-10-01 Glaxo Group Limited 1-imidazolgemethyl benzofuran derivatives as inhibitors of angiotensin ii activity
EP0514192A1 (en) * 1991-05-16 1992-11-19 Glaxo Group Limited Antihypertensive benzofuran derivatives, substituted by varied N-pyrimidinyl- or N-imidazolyl-methyl groups
US5252593A (en) * 1991-05-16 1993-10-12 Glaxo Group Limited Pyrazole containing benzofuran derivatives and pharmaceutical compositions
US5332831A (en) * 1991-05-16 1994-07-26 Glaxo Group Limited Benzofuran derivatives
US5374721A (en) * 1992-10-14 1994-12-20 Merck & Co., Inc. Benzo-fused lactams promote release of growth hormone
US20020128290A1 (en) * 1995-05-19 2002-09-12 Etsuo Ohshima Derivatives of benzofuran or benzodioxole
WO2000078726A1 (en) * 1999-06-18 2000-12-28 Eli Lilly And Company Imidazoline derivatives for the treatment of diabetes, especially type ii diabetes

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Application publication date: 20190920