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7-alkyl-N-pyrimidylindoline compound and synthesis method thereof

A compound, indoline technology, applied in the field of preparation of 7-alkyl-N-pyrimidine indoline compounds, can solve problems such as few reports, and achieve the effect of enriching the types of functional grouping reactions

Active Publication Date: 2019-01-11
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, the research on the functionalization reaction of indoline has become more and more mature, but there are few reports on the ring-opening alkylation reaction of indoline with vinylcyclopropane

Method used

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  • 7-alkyl-N-pyrimidylindoline compound and synthesis method thereof
  • 7-alkyl-N-pyrimidylindoline compound and synthesis method thereof
  • 7-alkyl-N-pyrimidylindoline compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The structural formula of the compound (E)-2-(4-(1-(2-pyrimidinyl) 7-indolinyl) 2-buten-1-yl) diethyl malonate of the present embodiment is:

[0025]

[0026] The preparation method is: under argon protection environment, add 0.2mmol of N-pyrimidine indoline compound, 0.3mmol of ethylene cyclopropane compound, 0.002mmol of [Cp*Rh(CH 3 EN) 3 ](SbF 6 ) 2 , 0.04mmol 1-adamantanecarboxylic acid, 0.02mmol silver hexafluoroantimonate, methanol 2mL, react at 90°C for 12 hours; , eluent: ethyl acetate / petroleum ether gradient elution, the ratio is from 0 / 100 to 100 / 0), and dried to obtain a light yellow oil with a yield of 88%, E / Z=20:1. 1 H NMR (400MHz, CDCl 3 )δ8.46–8.36(m,2H),7.13–6.98(m,3H),6.72–6.64(m,1H),5.69-5.59(m,1H),5.44-5.35(m,1H),4.45– 4.36(m,2H),4.21–4.12(m,4H),3.41–3.19(m,3H),3.05(t,J=7.6Hz,2H),2.66–2.53(m,2H),1.27-1.16( m,6H). 13 C NMR (101MHz, CDCl 3 )δ169.0, 161.3, 157.7, 142.3, 134.7, 131.7, 130.5, 128.2, 127.1, 124.2, 122.3, 112.2, 61.3, 53.2, 52.2...

Embodiment 2

[0028] Compound (E)-2-(4-(2-methyl-1-(2-pyrimidinyl) 7-indolinyl) 2-buten-1-yl) diethyl malonate The structural formula is:

[0029]

[0030] The preparation method is: under argon protection environment, add 0.2mmol of N-pyrimidine indoline compound, 0.3mmol of ethylene cyclopropane compound, 0.002mmol of [Cp*Rh(CH 3 EN) 3 ](SbF 6 ) 2 , 0.02mmol 1-adamantanecarboxylic acid, 0.04mmol silver hexafluoroantimonate, methanol 0.5mL, react at 90°C for 12 hours; Mesh, eluent: gradient elution with ethyl acetate / petroleum ether, the ratio is from 0 / 100 to 100 / 0), and dried to give a light yellow oil with a yield of 78%, E / Z=12:1. 1 H NMR (600MHz, CDCl 3 )δ8.43–8.37(m,2H),7.09–7.00(m,3H),6.67(t,J=4.2Hz,1H),5.64–5.56(m,1H),5.37–5.28(m,1H) ,4.98-4.95(m,1H),4.20-4.07(m,4H),3.48-3.16(m,4H),2.54(m,3H),1.36(t,J=8.7Hz,3H),1.25-1.21 (m,6H). 13 C NMR (101MHz, CDCl 3)δ169.0, 160.8, 157.6, 140.7, 133.5, 131.8, 130.8, 128.3, 126.9, 124.1, 122.9, 112.2, 61.3, 60.4, 52.2, 37.1, 36.9, 31....

Embodiment 3

[0032] Compound (E)-2-(4-(3-methyl-1-(2-pyrimidinyl) 7-indolinyl) 2-buten-1-yl) diethyl malonate The structural formula is:

[0033]

[0034] The preparation method is: under argon protection environment, add 0.2mmol of N-pyrimidine indoline compound, 0.3mmol of ethylene cyclopropane compound, 0.016mmol of [Cp*Rh(CH 3 EN) 3 ](SbF 6 ) 2 , 0.06mmol 1-adamantanecarboxylic acid, 0.02mmol silver hexafluoroantimonate, methanol 0.5mL, react at 90°C for 12 hours; Mesh, eluent: gradient elution with ethyl acetate / petroleum ether, the ratio is from 0 / 100 to 100 / 0), and dried to give a light yellow oil with a yield of 77%, E / Z=15:1. 1 H NMR (400MHz, CDCl 3 )δ8.45–8.37(m,2H),7.08-7.01(m,3H),6.70-6.66(m,1H),5.69-5.60(m,1H),5.43-5.36(m,1H),4.65– 4.56(m,1H),4.21–4.12(m,4H),3.91–3.84(m,1H),3.42–3.19(m,4H),2.59(t,J=7.0Hz,2H),1.28–1.21( m, 9H). 13 C NMR (101MHz, CDCl 3 )δ169.0, 161.5, 157.7, 142.0, 139.9, 131.7, 130.4, 128.3, 127.2, 124.4, 121.1, 112.2, 61.3, 61.0, 52.2, 36.8, 36.5,...

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Abstract

The invention discloses a 7-alkyl-N-pyrimidylindoline compound and a synthesis method thereof. The 7-alkyl-N-pyrimidylindoline compound has a general structural formula shown in the description. The synthesis method comprises: adding an N-pyrimidylindoline compound and a vinyl cyclopropane compound into a reaction tube in an argon environment, adding 1-adamantanecarboxylic acid, [Cp*Rh(CH3CN)3](SbF6)2 and silver hexafluoroantimonate into the reaction tube, then adding methanol into the reaction tube, carrying out a reaction process at 80-120 DEG C for 12h, and then carrying out leaching, thinlayer chromatographic separation and drying to obtain a desired product. The metal ruthenium (III) is used as a catalyst and methanol is used as a reaction solvent so that the carbon-carbon bond cleavage of vinylcyclopropane and activation of a 7-site carbon-hydrogen bond of an indoline compound are realized. The long alkyl chain with double bonds realizes a further functionalization reaction. Thesynthesis method is simple and efficient and has good selectivity. The 7-alkyl-N-pyrimidylindoline compound is easy to purify.

Description

technical field [0001] The invention belongs to the technical field of synthesis and application of organic compounds, and in particular relates to a preparation method of 7-alkyl-N-pyrimidine indoline compounds. Background technique [0002] Indoline, also known as 2,3-dihydroindole, is a product obtained by hydrogenation of indole at the 2 and 3 positions. It is an aromatic bicyclic organic heterocyclic compound (Comprehensive Heterocyclic Chemistry III). Indoline derivatives are characteristic structural fragments of many natural products and new drugs with biological activity, and their derivatives have good biological activities: for example, antiarrhythmic effect, treatment of glaucoma, prevention and treatment of cerebral ischemia, antitumor, etc. ( Org. Lett. 2014, 3, 345-348; J. Am. Chem. Soc. 2009, 131, 8758-8759; Org. Lett. 2003, 5, 269-271; Org. Lett. 2007, 9, 279-282). Among them, several classes of drugs have been successfully marketed, such as Pentopril (Pent...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/04
CPCC07D403/04
Inventor 朱新举王秋灵支昌磊李静刘爽赵雪梅郝新奇宋毛平
Owner ZHENGZHOU UNIV
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