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Polysubstituted 2-pyrrolopyridine derivative and preparation method thereof

A technology of pyrrole pyridine and multi-substitution, which is applied in the field of multi-substituted 2-pyrrole pyridine derivatives and its preparation, can solve the problems of difficulty in synthesizing multi-substituted 2-pyrrole pyridine derivatives, metal residues in products, limited use, etc., and achieve The effect of strong reaction specificity, mild reaction conditions and short reaction time

Active Publication Date: 2015-03-25
HUAQIAO UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are many problems in these methods: 1) the above-mentioned methods all use pyridine or polysubstituted pyridines as raw materials, and the raw materials are highly toxic, and some polysubstituted pyridines are difficult to obtain; Metal residues, limited use in the pharmaceutical industry; 3) It is difficult to synthesize multi-substituted 2-pyrrole pyridine derivatives, especially highly selective synthesis of multi-substituted 2-pyrrole pyridine derivatives

Method used

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  • Polysubstituted 2-pyrrolopyridine derivative and preparation method thereof
  • Polysubstituted 2-pyrrolopyridine derivative and preparation method thereof
  • Polysubstituted 2-pyrrolopyridine derivative and preparation method thereof

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Effect test

Embodiment 1

[0023] Preparation of 2-(3-benzoyl-2-phenyl-4-methylpyrrole-1-)-4,6-diphenyl-3-methylpyridine

[0024]

[0025] Add 0.5mmol of 1,3-diphenyl-3-(prop-2-yne-1-amino)prop-2-en-1-one, 1mmol of potassium hydroxide, and 1.5mL of acetonitrile into a 10mL reaction tube, and place In an oil bath at 120°C, react for 0.5h. Stop the reaction and cool to room temperature. The reaction solution was diluted with ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 Dried, filtered, concentrated, and purified by column chromatography to obtain 114.7 mg of the target product with a yield of 91%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, CDCl 3 )δ8.03(d,J=7.4Hz,2H),7.50–7.41(m,4H),7.24(dd,J=7.9,3.1Hz,2H),7.21–7.13(m,2H),7.03–6.84 (m,9H),6.82(d,J=7.4Hz,1H),2.43(s,3H),2.31(s,3H),1.41(s,3H),0.86(d,J=6.8Hz,3H) . 13 C NMR (101MHz, CDCl3) δ196.0, 154.0, 153.3, 151.3, 140.4, 139., 138.4, 138.1, 136.8, 135.0, 13...

Embodiment 2

[0027] Preparation of 2-(3-o-tolyl-2-phenyl-4-methylpyrrole-1-)-4-o-tolyl-6-phenyl-3-methylpyridine

[0028]

[0029] Add 0.5mmol of 1-o-tolyl-3-phenyl-3-(prop-2-yne-1-amino)prop-2-en-1-one, 1mmol of NaOH, and 5mL of acetonitrile into a 10mL reaction tube, and place In an oil bath at 80°C, react for 0.5h. Stop the reaction and cool to room temperature. The reaction solution was diluted with ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 Dry, filter, concentrate, and purify by column chromatography to obtain 103.7 mg of the target product with a yield of 78%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, CDCl 3 )δ8.03(d,J=7.4Hz,2H),7.50–7.41(m,4H),7.24(dd,J=7.9,3.1Hz,2H),7.21–7.13(m,2H),7.03–6.84 (m,9H),6.82(d,J=7.4Hz,1H),2.43(s,3H),2.31(s,3H),1.41(s,3H),0.86(d,J=6.8Hz,3H) ; 13 C NMR (101MHz, CDCl 3 )δ196.0, 154.0, 153.3, 151.3, 140.4, 139., 138.4, 138.1, 136.8, 135.0, 131.3, 130.3,...

Embodiment 3

[0031] Preparation of 2-(3-p-tolyl-2-phenyl-4-methylpyrrole-1-)-4-p-tolyl-6-phenyl-3-methylpyridine

[0032]

[0033] Add 0.5mmol of 1-p-tolyl-3-phenyl-3-(prop-2-yne-1-amino)prop-2-en-1-one, 1mmol of potassium tert-butoxide and 3mL of dimethylsulfoxide to 10mL In a reaction tube, placed in an oil bath at 50°C, reacted for 1 h. Stop the reaction and cool to room temperature. The reaction solution was diluted with ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 Dry, filter, concentrate, and purify by column chromatography to obtain 66.2 mg of the target product with a yield of 49%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, CDCl 3 )δ8.02(d, J=7.7Hz, 2H), 7.60(d, J=7.5Hz, 3H), 7.46(dt, J=14.4, 7.1Hz, 3H), 7.17(d, J=7.9Hz, 2H), 7.06–6.88(m,10H), 2.36(s,3H), 2.27(s,3H), 2.23(s,3H), 1.59(s,3H); 13 C NMR (100MHz, CDCl 3 )δ1945,154.0,153.1,151.9,142.1,138.3,138.1,137.0,136.6,135.9,131.7,1...

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Abstract

The invention discloses a polysubstituted 2-pyrrolopyridine derivative. The derivative has a structure shown in a formula in the specification, wherein in the formula, R1, R2, R3, R4, R5, R6, R7 and R8 are selected from any one of hydrogen atoms, halogen atoms, alkyl, aryl, substituted aryl, acyl, amino, nitro and alkoxy. The invention also discloses a preparation method of the polysubstituted 2-pyrrolopyridine derivative. The polysubstituted 2-pyrrolopyridine derivative shown in the formula is obtained at high yield after completing heating reaction of N-propargyl enaminone in a solvent in the presence of appropriate alkali. The polysubstituted 2-pyrrolopyridine derivative and the preparation method have the beneficial effects that the reaction conditions are mild; the reaction time is short; the range of substrates is wide; the reaction specificity is strong; the yield is high; aftertreatment is simple and convenient to carry out.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to multi-substituted 2-pyrrole pyridine derivatives and a preparation method thereof. Background technique [0002] Multi-substituted 2-pyrrole pyridine derivatives are a class of organic synthesis intermediates with a wide range of uses, and have important application values ​​in natural products, pharmaceutical production, organic synthesis, and material science. Therefore, the research on new synthesis methods of multi-substituted 2-pyrrolopyridines has important application value and has attracted the attention of researchers in related fields. [0003] The traditional synthesis methods of 2-pyrrolopyridine derivatives include the condensation reaction of 2-aminopyridine and 1,4-dicarbonyl compound, and the copper-catalyzed coupling reaction of 2-halopyridine and amine compound. However, there are many problems in these methods: 1) the above-mentioned methods all use ...

Claims

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Application Information

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IPC IPC(8): C07D401/04C07D409/14
CPCC07D401/04C07D409/14
Inventor 崔秀灵沈金海
Owner HUAQIAO UNIVERSITY
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