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Fluorine methyl -containing compound and preparation method thereof

A compound and methyl technology, which is applied in the field of fluoromethyl-containing compounds and their preparation, can solve the problems of expensive preparation methods, poor functional group compatibility, and difficult preparation

Active Publication Date: 2019-04-30
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The technical problem to be solved by the present invention is to overcome the disadvantages of difficult preparation of fluoromethyl-containing compounds in the prior art, and the preparation method is expensive, the amount of catalyst used is high, the compatibility of functional groups is poor, and the compatibility of aromatic heterocyclic substrates is poor. A kind of compound containing fluoromethyl group and preparation method thereof

Method used

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  • Fluorine methyl -containing compound and preparation method thereof
  • Fluorine methyl -containing compound and preparation method thereof
  • Fluorine methyl -containing compound and preparation method thereof

Examples

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preparation example Construction

[0172] The preparation method of nickel complex containing ligand coordination:

[0173] (4,4’-di-tBu-bpy)NiCl 2 :(Angew.Chem.Int.Ed.2016,55,5837-41.)

[0174]

[0175] Add anhydrous NiCl to a 100mL three-neck flask 2 (129.6 mg, 1.0 mmol) in 13 mL of an ethanolic solution, to which was added 7 mL of an ethanolic solution of 4,4'-ditBu-bpy (271 mg, 1.0 mmol), the reaction solution was heated to reflux for 10 h, the reaction solution was filtered, and the filtrate was concentrated to obtain Green solid 358 mg (90% yield), the solid was recrystallized from methanol.

[0176] (4,4’-di-NH 2 -bpy)NiCl 2 :

[0177]

[0178] Add anhydrous NiCl to the 25mL reaction flask 2 (129.6 mg, 1.0 mmol) in 5 mL of methanol, to which was added 4,4'-ditNH 2 - 5 mL of methanol solution of bpy (186.2 mg, 1.0 mmol), the reaction solution was heated at 80°C for 10 h, the reaction solution was filtered, and the filtrate was concentrated to obtain a green solid. The solid was recrystallize...

Embodiment 1

[0186]

[0187] Method 1: 36.7 mg of the target product was obtained with a yield of 90%; the purity was identified by hydrogen spectrum as more than 95%.

[0188] 1 H NMR (400MHz, CDCl 3 )δ7.72-7.68(m, 2H), 7.64-7.59(m, 4H), 7.52-7.47(m, 2H), 7.44-7.49(m, 1H), 6.71(t, J=56.4Hz, 1H) . 19 F NMR (376MHz, CDCl 3 )δ-110.3(d, J=56.5Hz, 2F). 13 C NMR (125.7MHz, CDCl 3 )δ143.7(t,J=2.0Hz),140.2,133.2(t,J=22.4Hz),128.9,127.9,127.4,127.2,126.0(t,J=6.0Hz),114.7(t,J=238.5 Hz).

Embodiment 2

[0190]

[0191] Method 1: 36 mg of the target product was obtained with a yield of 87%; the purity was identified by hydrogen spectrum as more than 95%.

[0192] 1 H NMR (400MHz, CDCl 3 )δ7.76(s,1H),7.73(d,J=7.3Hz,1H),7.63(d,J=7.5Hz,2H),7.59–7.45(m,4H),7.41(t,J=7.3 Hz,1H),6.73(t,J=56.5Hz,1H). 19 F NMR (376MHz, CDCl 3 )δ-110.6(d, J=56.5Hz, 2F). 13 C NMR (101MHz, CDCl 3 )δ141.8,140.1,134.9(t,J=22.2Hz),129.4(t,J=1.9Hz),129.2,128.9,127.8,127.2,124.3(t,J=6.0Hz),124.3(t,J=6.0 Hz), 114.7(t, J=238.9Hz).

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Abstract

The invention discloses a fluorine methyl -containing compound and a preparation method thereof. The fluorine methyl-containing compound is as shown in a formula C, R is a group containing an aryl group, or a group containing a heteroaryl group, the aromatic carbon atoms on the aryl group or the heteroaryl group are connected with CFmHn, m is 1 or 2, and m + n is equal to 3. The compound is difficult to prepare according to the prior art, raw materials and a catalyst of the preparation method are common industrial raw materials, and are cheap and easy to obtain, the preparation method is highin reaction efficiency, high in yield, simple in post-treatment, low in toxicity, environment-friendly, good in functional group compatibility, wide in broad-spectrum property, low in production costand good in market application prospect.

Description

technical field [0001] The present invention relates to a compound containing fluorine methyl group and a preparation method thereof. Background technique [0002] Compounds containing difluoromethyl substituted aryl or heteroaryl structures have a very wide range of applications in the fields of medicine and pesticides. Due to the unique properties of fluorine, the introduction of difluoromethyl into the aromatic ring can not only increase the lipid solubility of the compound, but also effectively improve the metabolic stability of the benzylic position of the aryl group. The ability of large compounds to bind to the target, so the introduction of difluoromethyl groups into aryl groups has become a common means of drug molecule design. [0003] The traditional method for synthesizing compounds containing difluoromethyl substituted aryl structures is mainly to use deoxyfluorination reagents such as DAST (ie, diethylaminosulfur trifluoride) to deoxyfluoride carbonyl compound...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D223/16C07C22/08C07C17/263C07C43/225C07C41/22C07D317/52C07D295/205C07C69/76C07C45/63C07C49/80C07C255/40C07C317/14C07C69/65C07C33/46C07F5/02C07D213/64C07D213/80C07D213/803C07D263/57C07D277/66C07C255/35C07D213/26C07D279/30C07D495/04C07D215/12C07C69/712C07D333/76C07D307/91C07D471/04C07D239/26
CPCC07C22/08C07C33/46C07C43/225C07C49/80C07C69/65C07C69/712C07C69/76C07C255/35C07C255/40C07C317/14C07D213/26C07D213/64C07D213/80C07D213/803C07D215/12C07D223/16C07D239/26C07D263/57C07D277/66C07D279/30C07D295/205C07D307/91C07D317/52C07D333/76C07D471/04C07D495/04C07F5/025Y02P20/584
Inventor 张新刚徐畅郭文豪
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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