Synthesis method for 3-(trifluoroacetyl)indole derivative

A technology of indole derivatives and synthesis methods, which is applied in the field of synthesizing 3-indole derivatives by carbon-hydrogen bond functionalization reaction, can solve the problems that have not been reported in the literature, and achieve high yield, economical raw materials, and easy operation. simple effect

Active Publication Date: 2017-07-14
江西景华生态科技股份有限公司
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Problems solved by technology

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  • Synthesis method for 3-(trifluoroacetyl)indole derivative
  • Synthesis method for 3-(trifluoroacetyl)indole derivative
  • Synthesis method for 3-(trifluoroacetyl)indole derivative

Examples

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Effect test

Embodiment 1

[0015] Example 1: Synthesis of 3-(trifluoroacetyl)-1-methylindole

[0016]

[0017] Add dimethyl sulfoxide (2 mL) to a 25 mL pressure-resistant reaction tube, N - Methylindole (39.3 mg, 0.3 mmol), ethyl trifluoropyruvate (102.0 mg, 0.6 mmol), cuprous chloride (44.78 mg, 1.5 eq.), magnetically stirred in an oil bath at 80 °C for 12 Hour. After the reaction was completed, most of the solvent was evaporated under reduced pressure, and the remaining mixed solution was separated and purified by column chromatography with petroleum ether / ethyl acetate (10:1) as the eluent to obtain the desired product, which was light yellow Solid, 57.9 mg, yield 85%.

[0018] Its NMR data are as follows:

[0019] 1 H NMR (300 MHz, CDCl 3 ) δ= 8.04−8.02 (m, 1H), 7.30−7.27 (m, 3H), 3.68(s, 3H), 2.73 (s, 3H); 13 C NMR (CDCl 3 , 75 MHz) δ= 175.0 (q, J CF = 35.6 Hz), 150.2, 136.7, 125.0, 123.1, 121.5, 120.6 (q, J CF = 4.3 Hz), 117.2 (q, J CF =288.0 Hz), 109.7, 107.6, 29.7, 12.9.

Embodiment 2

[0020] Example 2: Synthesis of 3-(trifluoroacetyl)indole

[0021]

[0022] Add dimethyl sulfoxide (2 mL), indole (35.1 mg, 0.3 mmol), ethyl trifluoropyruvate (102.0 mg, 0.6 mmol), cuprous chloride (44.78 mg, 1.5 eq.), and reacted for 12 hours in an 80°C oil bath with magnetic stirring. After the reaction was completed, most of the solvent was evaporated under reduced pressure, and the remaining mixed solution was separated and purified by column chromatography with petroleum ether / ethyl acetate (10:1) as the eluent to obtain the desired product, which was light yellow Solid, 35.8 mg, yield 56%.

[0023] Its NMR data are as follows:

[0024] 1 H NMR (300 MHz, CDCl 3 ) δ =12.75 (s, 1 H), 8.49 (s, 1 H), 8.20 (d, J =5.6 Hz, 1 H), 7.60 (d, J = 6.4 Hz, 1 H), 7.36−7.30 (m , 2 H); 13 C NMR (DMSO-d 6 ,75 MHz) δ 174.0 (q, J CF = 33.6 Hz), 137.6 (q, J CF = 4.8 Hz), 136.7, 125.8,124.4, 123.5, 121.2, 117.0 (q, J CF = 289.8 Hz), 113.1, 108.9.

Embodiment 3

[0025] Example 3: Synthesis of 3-(trifluoroacetyl)-1-methyl-6-chloroindole

[0026]

[0027] Add dimethyl sulfoxide (2 mL) to a 25 mL pressure-resistant reaction tube, N -Methyl-6-chloroindole (49.5 mg, 0.3 mmol), ethyl trifluoropyruvate (102.0 mg, 0.6 mmol), cuprous chloride (44.78 mg, 1.5 eq.), in an oil bath at 80 °C The reaction was stirred magnetically for 12 hours. After the reaction was completed, most of the solvent was evaporated under reduced pressure, and the remaining mixed solution was separated and purified by column chromatography with petroleum ether / ethyl acetate (10:1) as the eluent to obtain the desired product, which was light yellow Solid, 55.6 mg, yield 71%.

[0028] Its NMR data are as follows:

[0029] 1 H NMR (300 MHz, CDCl 3 ) δ = 8.30 (d, J = 8.8 Hz, 1 H), 7.89 (s, 1 H), 7.39 (d, J = 1.6 Hz, 1 H), 7.34 (dd, J = 2.0 Hz, 2.0 Hz, 1 H), 3.88 (s, 3 H); 13 C NMR (CDCl 3 , 75 MHz) δ= 174.7 (q, J CF = 34.9 Hz), 138.7 (q, J CF = 4.8 Hz), 137.8,...

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Abstract

The invention discloses a synthesis method for a 3-(trifluoroacetyl)indole derivative and belongs to the technical field of organic synthesis intermediates. The method particularly includes the following steps: 1) feeding dimethyl sulfoxide, an indole derivative, ethyl trifluoropyruvate and cuprous chloride into a pressure-resistant reaction tube, tightly screwing a plug of the reaction tube, and performing a magnetic-stirring reaction for 12 h in oil bath at 80 DEG C; 2) when the reaction is finished, performing extraction with ethyl ether and mixing organic phases, performing pressure reduced evaporation to remove most of the solvent, and performing column chromatography separation and purification to residual mixture liquid with petroleum ether and ethyl acetate, volume ratio being 5:1-10:1, as a leaching liquid, thereby producing the product. The 3-(trifluoroacetyl)indole derivative has wide applications in the fields such as medicines, pesticides, etc. The synthesis method is low in cost, has simple operations and high yield, and has excellent application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis intermediates, and in particular relates to a method for synthesizing 3-(trifluoroacetyl)indole derivatives by using a carbon-hydrogen bond functionalization reaction. Background technique [0002] 3-(trifluoroacetyl) indole derivatives are very important intermediates in organic synthesis ( Eur. J. Org. Chem. 2014, 2014 , 3981; Tetrahedron Lett. 2013, 54 , 7202; Tetrahedron: Asymmetry 2013, 24 , 1369), and is also an important skeleton of many physiologically active natural products and drugs ( J. Med. Chem. 2014, 57 , 7472; ACS Med. Chem. Lett. 2014, 5 , 863). The traditional synthesis methods of these compounds mainly include: ① Friedel−Crafts acylation reaction, using trifluoroacetyl chloride or trifluoroacetic anhydride as a trifluoroacetylation reagent, and electron-rich indole derivatives as nucleophiles to efficiently synthesize 3 -(trifluoroacetyl)indole deriv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/12
CPCC07D209/12
Inventor 严国兵黄达云何平曹晰晗郑万彬柯求敏沈旭茜
Owner 江西景华生态科技股份有限公司
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