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Preparation method of o-aryl benzamide compound

A technology for arylbenzamide and ketone compounds, which is applied in the field of preparation of o-arylbenzamide compounds, can solve the problems of inconvenient use and operation of organometallic reagents, achieve fewer reaction steps and reduce the loss of raw materials , the effect of wide applicability

Pending Publication Date: 2022-08-02
绍兴久孚新材料科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Ortho-arylbenzamides are important organic synthesis reagents. In the prior art, most routes need to use pre-prepared organometallic reagents (organozinc reagents, organomagnesium reagents, organoboron reagents, etc.), these organometallic reagents extremely inconvenient to use and operate

Method used

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  • Preparation method of o-aryl benzamide compound
  • Preparation method of o-aryl benzamide compound
  • Preparation method of o-aryl benzamide compound

Examples

Experimental program
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Effect test

Embodiment 1

[0059] 3-Toluo[d][1,2,3]triazin-4(3H)-one (16.1 mg, 0.10 mmol), bromobenzene (21 μL, 0.2 mmol), nickel diethyl bromide in a glove box Glycol dimethyl ether (3.5mg, 0.001mmol), bipy2,2'-bipyridine (2.3mg, 0.0015mmol) and zinc powder (1.31g, 0.2mmol) were added to a microwave tube, followed by 0.2mL N,N - Dimethylacetamide, capped and removed from the glove box.

[0060] Then refluxed at 80°C for 12 hours, cooled to room temperature, opened the lid and added three drops of water to quench the reaction, removed the solvent under reduced pressure, and separated the crude product by column chromatography (petroleum ether:ethyl acetate=5:1) to obtain N-methyl-[1,1'-biphenyl]-2-carboxamide (18.4 mg, 87% yield).

[0061] The hydrogen and carbon NMR spectra of the product are figure 1 and figure 2 , the spectral data is: 1 H NMR (400MHz, CDCl 3 )δ: 7.66(d, J=8.1Hz, 1H), 7.49-7.45(m, 1H), 7.42-7.36(m, 5H), 7.38-7.35(m, 2H), 5.30(s, 1H), 2.66 (d,J=4.9Hz,3H)ppm. 13 C{ 1 H}NMR (10...

Embodiment 2

[0063] In a glove box, combine 3-Toluo[d][1,2,3]triazin-4(3H)-one (16.1 mg, 0.10 mmol), 4-tert-butylbromobenzene (35 μL, 0.2 mmol), Nickel bromide diethylene glycol dimethyl ether (3.5 mg, 0.001 mmol), bipy (2.3 mg, 0.0015 mmol) and zinc powder (1.31 g, 0.2 mmol) were added to a microwave tube, followed by 0.2 mL of N,N-bismuth Methylacetamide, capped and removed from the glove box.

[0064] Then refluxed at 80°C for 12 hours, cooled to room temperature, opened the lid and added three drops of water to quench the reaction, removed the solvent under reduced pressure, and separated the crude product by column chromatography (petroleum ether:ethyl acetate=5:1) to obtain 4'-(tert-Butyl)-N-methyl-[1,1'-biphenyl]-2-carboxamide (24.1 mg, 90% yield).

[0065] The hydrogen and carbon NMR spectra of the product are image 3 and Figure 4 , the spectral data is: 1 H NMR (400MHz, CDCl 3 )δ: 7.69-7.67(m, 1H), 7.47-7.42(m, 3H), 7.40-7.33(m, 4H), 5.22(s, 1H), 2.67(d, J=4.9Hz, 3H), 1.35 ...

Embodiment 3

[0067] In a glove box, combine 3-Toluo[d][1,2,3]triazin-4(3H)-one (16.1 mg, 0.10 mmol), 4-methoxybromobenzene (25 μL, 0.2 mmol), Nickel bromide diethylene glycol dimethyl ether (3.5 mg, 0.001 mmol), bipy (2.3 mg, 0.0015 mmol) and zinc powder (1.31 g, 0.2 mmol) were added to a microwave tube, followed by 0.2 mL of N,N-bismuth Methylacetamide, capped and removed from the glove box.

[0068] Then refluxed at 80°C for 12 hours, cooled to room temperature, opened the lid and added three drops of water to quench the reaction, removed the solvent under reduced pressure, and separated the crude product by column chromatography (petroleum ether:ethyl acetate=5:1) to obtain 4'-(Methoxy)-N-methyl-[1,1'-biphenyl]-2-carboxamide (22.0 mg, 91% yield).

[0069] The hydrogen and carbon NMR spectra of the product are Figure 5 and Image 6 , the spectral data are: 7.68–7.63(m,1H), 7.46–7.42(m,1H), 7.38–7.31(m,4H), 6.97–6.93(m,2H), 5.29(s,1H), 3.84 (s,3H),2.70(d,J=4.9Hz,3H)ppm. 13 C{ 1 H}N...

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Abstract

The invention discloses a preparation method of an o-aryl benzamide compound, which comprises the following steps: mixing a 1, 2, 3-benzotriazine-4-(3H)-ketone compound and an aryl bromide with an organic solvent under the action of a transition metal catalyst and a reducing agent, and carrying out reduction cross-coupling reaction to prepare the o-aryl benzamide compound. The 1, 2, 3-benzotriazine-4-(3H)-ketone compound and aryl bromide are used as raw materials, the zinc powder is used as a reducing agent, nickel bromide diethylene glycol dimethyl ether is used as a catalyst, then a series of o-aryl benzamide compounds are prepared, and the synthesis method is simple, economical, environmentally friendly, wider in applicability and suitable for large-scale production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of an o-arylbenzamide compound. Background technique [0002] Transition metal-catalyzed reductive cross-coupling reactions are one of the important means to construct carbon-carbon bonds and carbon-heterobonds, and are widely used in the synthesis of drug molecules and natural products. [0003] The reductive cross-coupling reaction between two different electrophiles catalyzed by transition metals has good functional group tolerance, which can avoid the use of water- and air-sensitive organometallic reagents and simplify the traditional process. [0004] O-arylbenzamide compounds are important organic synthesis reagents. In the prior art, most routes need to use pre-prepared organometallic reagents (organozinc reagents, organomagnesium reagents, organoboron reagents, etc.), these organometallic reagents. It is extremely inconvenient to use and ...

Claims

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Application Information

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IPC IPC(8): C07C231/10C07C233/65C07C235/42
CPCC07C231/10C07C233/65C07C235/42Y02P20/584
Inventor 毛建友崔小刚
Owner 绍兴久孚新材料科技有限公司
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