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Monofluoroalkyl-containing compound and its preparation method and use

A monofluoroalkyl and compound technology, which is applied in the preparation of carbon-based compounds, the preparation of organic compounds, and steroid compounds, etc., can solve the problems of unsuitability for industrial production, long reaction steps, and low reaction conversion rate.

Active Publication Date: 2017-01-04
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The technical problem to be solved by the present invention is to overcome the cumbersome reaction steps, poor functional group compatibility, expensive catalyst, high dosage, harsh reaction conditions, long reaction steps, and reaction conversion rate of the preparation method of the compound containing a fluoroalkyl group in the prior art. Low, low yield, not suitable for industrial production and other defects provide a compound containing a fluoroalkyl, its preparation method and application

Method used

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  • Monofluoroalkyl-containing compound and its preparation method and use
  • Monofluoroalkyl-containing compound and its preparation method and use
  • Monofluoroalkyl-containing compound and its preparation method and use

Examples

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Embodiment 1

[0055]

[0056] In a 25mL reaction tube, add 178mg (0.9mmol) 4-biphenylboronic acid, 6.6mg (5mol%, mol% refers to NiCl 2 The percentage of DME and the molar weight of compound B) NiCl 2 DME (Nickel Dimethyl Ethylene Ether Chloride), 5.4mg (5mol%, mol% refers to the percentage of phen and compound B molar weight) phen (1,10'-phenanthroline), 7.4mg (5mol %, mol% refers to the percentage of DMAP and compound B molar weight) DMAP (4-dimethylaminopyridine), 166mg (1.2mmol) K 2 CO 3 , 2mL ethylene glycol dimethyl ether, 1.7mL 1,4-dioxane, inject 300uL CH 2 The 1,4-dioxane solution of FBr (concentration: 2M, 0.6mmol), after stirring at 70°C for 24 hours, the isolated yield was 90%, and the purity was greater than 95% as identified by hydrogen spectroscopy. 1 H NMR (400MHz, CDCl 3 )δ7.61-7.69(m, 4H), 7.45-7.52(m, 4H), 7.40(t, J=7.3Hz, 1H), 5.45(d, J=47.9Hz, 2H). 13 C NMR (100MHz, CDCl 3 )δ141.7(d, J=3.2Hz), 140.6(d, J=1.1Hz), 135.1(d, J=17.1Hz), 128.8, 128.0(d, J=5.7Hz), 127....

Embodiment 2

[0058]

[0059] To a 25mL reaction tube, add 195mg (0.9mmol) 2-fluorobiphenyl-4-boronic acid, 6.6mg (5mol%, mol% refers to NiCl 2 The percentage of DME and the molar weight of compound B) NiCl 2 DME (Nickel Dimethyl Ethylene Ether Chloride), 5.4mg (5mol%, mol% refers to the percentage of phen and compound B molar weight) phen (1,10'-phenanthroline), 7.4mg (5mol %, mol% refers to the percentage of DMAP and compound B molar weight) DMAP (4-dimethylaminopyridine), 166mg (1.2mmol) K 2 CO 3 , 2mL ethylene glycol dimethyl ether, 1.7mL 1,4-dioxane, inject 300uL CH 2 The 1,4-dioxane solution of FBr (concentration: 2M, 0.6mmol) was stirred at 70°C for 24 hours, the isolated yield was 83%, and the purity was greater than 95% as identified by hydrogen spectroscopy. 1 H NMR (400MHz, CDCl 3 )δ7.58-7.53 (m, 2H), 7.50-7.44 (m, 3H), 7.43-7.37 (m, 1H), 7.24-7.17 (m, 2H), 5.42 (d, J=47.5Hz, 1H) . 13 C NMR (125.7MHz, CDCl 3 )δ159.7 (d, J=249.0Hz), 137.5 (dd, J=17.6, 7.7Hz), 135.3, 131....

Embodiment 3

[0061]

[0062] In a 25mL reaction tube, add 178mg (0.9mmol) 3-biphenylboronic acid, 13.2mg (10mol%, mol% refers to NiCl 2 The percentage of DME and the molar weight of compound B) NiCl 2 DME (nickel chloride dimethylethylene ether), 10.8mg (10mol%, mol% refers to the percentage of phen and compound B molar weight) phen (1,10'-phenanthroline), 14.4mg (10mol %, mol% refers to the percentage of DMAP and compound B molar weight) DMAP (4-dimethylaminopyridine), 166mg (1.2mmol) K 2 CO 3 , 2mL ethylene glycol dimethyl ether, 1.7mL 1,4-dioxane, inject 300uL CH 2 The 1,4-dioxane solution of FBr (concentration: 2M, 0.6mmol), after stirring at 70°C for 24 hours, the isolated yield was 90%, and the purity was greater than 95% as identified by hydrogen spectroscopy. 1 H NMR (400MHz, CDCl 3 )δ7.67-7.60(m, 4H), 7.54-7.46(m, 3H), 7.44-7.38(m, 2H), 5.48(d, J=47.8Hz, 2H). 13 C NMR (125.7MHz, CDCl 3 )δ141.6 (d, J=1.3Hz), 140.7, 136.7 (d, J=17.1Hz), 129.0 (d, J=1.1Hz), 128.8, 127.56, 12...

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Abstract

The invention discloses a monofluoroalkyl-containing compound and its preparation method. The preparation method comprises that in a solvent, in the presence of an alkali, an additive, a ligand and a catalyst, a compound A and a compound B undergo a suzuki coupling reaction to produce a compound C. The catalyst is a nickel salt with a chemical formula of NiLnCl2, NiLnBr2, NiLnI2 or NiQ2. mH2O. The preparation method introduces monofluoroalkyl through a one-step reaction, is efficient and simple, has good function group compatibility and good broad spectrum activity, is free of a highly toxic reagent, has simple and safe aftertreatment processes, is environmentally friendly, utilizes a small amount of a cheap catalyst, allows mild reaction conditions, realizes a high reaction conversion rate, a high yield and a low production cost and is suitable for industrial production.

Description

technical field [0001] The present invention relates to a compound containing a fluoroalkyl group, its preparation method and application. Background technique [0002] Fluoroalkyl-substituted arene compounds have important applications in the fields of medicine, pesticides and materials science. Although there are some reports on the introduction of fluoroalkyl groups to aromatic rings in recent years, there are few reports on the synthesis methods of compounds containing fluoroalkyl groups. [0003] Due to the unique physical, chemical and biological properties of fluorine atoms, this type of fluoroalkyl-containing compounds has very important applications in the field of life sciences ((a) B.E.Smart, J.Fluorine Chem.2001, 109, 3; (b ) P.Maienfisch, R.G.Hall, Chimia.2004, 58, 93; (c) Special issue on "Fluorine in the Life Sciences", ChemBioChem.2004, 5, 557; (d) F.Babudri, G.M.Farinola, F. Naso, R. Ragni, Chem. Commun. 2007, 1003; (e) K. Müller, C. Faeh, F. Diederich, Sc...

Claims

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Application Information

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IPC IPC(8): C07C45/63C07C49/80C07C47/55C07C17/26C07C22/04C07C25/13C07C67/307C07C69/767C07C253/30C07C255/50C07C315/04C07C317/14C07D295/26C07F7/08C07C41/22C07C43/20C07D307/79C07C43/275C07C319/20C07C321/28C07J1/00C07D491/056C07D211/96C07D213/74
CPCC07C17/26C07C22/04C07C25/13C07C67/307C07C69/76C07C45/63C07C49/80C07C47/55C07C253/30C07C255/50C07C315/04C07C317/14C07C41/22C07C43/20C07C43/275C07C319/20C07C321/28
Inventor 张新刚安伦
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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