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A kind of C2-sulfonamidoindole derivative and its preparation method

A technology of sulfonylaminoindole derivatives and sulfonyl azide, which is applied in the new synthesis field of indole derivatives, can solve the problems of excessive catalyst amount and low yield, and achieve simple and easy operation process and simple steps , The effect of reducing the reaction material

Active Publication Date: 2021-12-17
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to overcome a series of problems such as excessive amount of catalyst and low yield in the carboamination reaction in which indole participates, the primary purpose of the present invention is to provide a C2-sulfonamidoindole derivative and its preparation method

Method used

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  • A kind of C2-sulfonamidoindole derivative and its preparation method
  • A kind of C2-sulfonamidoindole derivative and its preparation method
  • A kind of C2-sulfonamidoindole derivative and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The preparation steps of C2-sulfonamidoindole derivatives are as follows:

[0040]

[0041] Add 1-(3-phenyl-1-(pyridin-2-yl)-1H-indol-2-yl)butan-1-ol (68 mg, 0.2 mmol), benzenesulfonyl azide (73 mg, 0.4mmol), [Cp * Rh(CH 3 EN) 3 ][SbF 6 ] 2 (10mg, 0.01mmol) and 1ml of anhydrous 1,2-dichloroethane, stirred and reacted at 85°C for 48h, stopped heating, cooled to room temperature, spin-dried, and further separated and purified by column chromatography to obtain 63mg of the product , Yield: 74%.

[0042] The structural characterization data of the product obtained in this embodiment are as follows:

[0043] 1 H NMR (500MHz, CDCl 3 )δ9.22(s,0.86H),8.56(d,J=4.5Hz,1H),7.74(t,J=7.7Hz,1H),7.67(d,J=7.9Hz,1H),7.43(d , J=8.2Hz, 1H), 7.30–7.24(m, 4H), 7.22–7.16(m, 5H), 7.12(s, 3H), 6.94(t, J=7.5Hz, 2H). figure 1 .

[0044] 13 C NMR (126MHz, CDCl 3 )δ149.9, 149.0, 139.5, 139.0, 133.9, 132.6, 132.2, 129.4, 129.0, 128.4, 128.3, 126.6, 126.6, 126.3, 124.1, 121.9, 121.6, ...

Embodiment 2

[0048] The preparation steps of C2-sulfonamidoindole derivatives are as follows:

[0049]

[0050] In a sealed tube add (3-phenyl-1-(pyrimidin-2-yl)-1H-indol-2-yl)methanol (69 mg, 0.2 mmol), p-toluenesulfonyl azide (80 mg, 0.4 mmol) , [Cp * Rh(CH 3 EN) 3 ][SbF 6 ] 2 (10mg, 0.01mmol) and 1ml of anhydrous 1,2-dichloroethane, stirred and reacted at 85°C for 48h, then stopped heating, cooled to room temperature, spin-dried, and further separated and purified by column chromatography to obtain 24mg of the product. Yield: 14%.

[0051] The structural characterization data of the product obtained in this embodiment are as follows:

[0052] 1 H NMR (400MHz, Chloroform-d) δ9.08(s, 0.86H), 8.53(d, J=4.8Hz, 2H), 8.29(d, J=8.3Hz, 1H), 7.60(d, J=7.9 Hz, 1H), 7.55–7.48(m, 2H), 7.30(t, J=7.5Hz, 2H), 7.26–7.18(m, 2H), 7.15(d, J=7.4Hz, 1H), 7.11(d , J=8.0Hz, 2H), 6.95(t, J=4.8Hz, 1H), 6.72(d, J=8.0Hz, 2H), 2.14(s, 3H). image 3 .

[0053] 13 C NMR (101MHz, CDCl 3 )δ157.8, 157.3...

Embodiment 3

[0058] The preparation steps of C2-sulfonamidoindole derivatives are as follows:

[0059]

[0060] Add 1-(3-phenyl-1-(pyridin-2-yl)-1H-indol-2-yl)butan-1-ol (68 mg, 0.2 mmol), thiophenesulfonyl azide (80 mg, 0.4mmol), [Cp * Rh(CH 3 EN) 3 ][SbF 6 ] 2 (10mg, 0.01mmol) and 1ml of anhydrous 1,2-dichloroethane, stirred and reacted at 85°C for 48h, then stopped heating, cooled to room temperature, spin-dried, and further separated and purified by column chromatography to obtain 72mg of the product. Yield: 84%.

[0061] The structural characterization data of the product obtained in this embodiment are as follows:

[0062] 1 H NMR (400MHz, Chloroform-d) δ9.17(s,0.91H),8.62(m,1H),7.84(m,1H),7.78(m,1H),7.55–7.49(m,3H),7.38 –7.31 (m, 4H), 7.30 – 7.21 (m, 4H), 6.91 (dd, J=3.8, 1.4Hz, 1H), 6.62 (dd, J=5.0, 3.8Hz, 1H). Figure 5 .

[0063] 13 C NMR (101MHz, CDCl 3 )δ150.0, 149.1, 140.0, 138.9, 133.8, 132.8, 132.4, 132.2, 129.5, 128.4, 127.1, 126.8, 126.7, 126.1, 124.3, 122.0...

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Abstract

The invention discloses a C2-sulfonamidoindole derivative and a preparation method thereof. The method comprises the following steps: mixing N-pyridine-α-indole aryl alcohol compound, sulfonyl azide and a catalyst, and then Add an organic solvent, react at 80-90°C, cool to room temperature after the reaction, and generate the C2-sulfonamidoindole derivative. The method of the invention is simple and efficient, and the raw materials used are cheap and non-toxic, and the preparation method optimizes the previous preparation method to make the reaction operation simpler. In addition, the whole experimental operation process is simple and easy, the steps are simple and convenient, and the product is also easier to purify.

Description

technical field [0001] The invention relates to a new synthesis method of indole derivatives, in particular to a C2-sulfonamido indole derivative and a preparation method thereof. Background technique [0002] C2-indole sulfonamide compound is an important skeleton of many drug molecules, and the development of its efficient preparation reaction is one of the research fields of organic synthetic chemistry that attracts much attention. So exploring new reaction types or different routes to synthesize this type of compounds is the direction that chemists are keen on. [0003] Alcohols have been well-applied as cheap and readily available industrial raw materials, and the selective amination of alcohols is considered to be a more attractive method for the synthesis of complex molecules. Such as (1) using fatty alcohol and methylsulfonimide as raw materials, under the action of strong alkali sodium hydride, by removing a molecule of N 2 Generate oxime ethers (Hassner, A.; Patc...

Claims

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Application Information

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IPC IPC(8): C07D401/04C07D403/04C07D409/14
CPCC07D401/04C07D403/04C07D409/14
Inventor 曾伟胡新伟
Owner SOUTH CHINA UNIV OF TECH
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