ChemicalBook CAS DataBase List ETHYL3-METHYL-2-INDOLECARBOXYLATE

ETHYL3-METHYL-2-INDOLECARBOXYLATE synthesis

10synthesis methods

Product Name:ETHYL3-METHYL-2-INDOLECARBOXYLATE
CAS Number:26304-51-8
Molecular formula:C12H13NO2
Molecular Weight:203.24

2142-69-0 Synthesis

2142-69-0
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$6.00/1g

105-56-6
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$10.00/5ml

26304-51-8
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$18.00/100mg

Yield: 49%

Reaction Conditions:

with copper(l) iodide;caesium carbonate in dimethyl sulfoxide at 50;Inert atmosphere;

Steps:

3.1 Step 1:
Preparation of ethyl 3-methyl-1H-indole-2-carboxylate

2-bromoacetophenone (3g, 15.07mmol), CuI (287mg, 1.51mmol) and cesium carbonate (9.82g, 30.14mmol) were added to 40mL of DMSO, and ethyl cyanoacetate was slowly added at 50 °C under protect of nitrogen.
After the reaction was completed, 40 mL of water was added, and ethyl acetate (3*50 mL) was added for extraction.
The combined organic layer was washed with water (3*30 mL) and saturated NaCl solution (50 mL), dried over anhydrous Na₂SO₄ and filtered.
The solvent was dried under reduced pressure, and the residue was isolated and purified by flash column chromatography (petroleum ether / ethyl acetate = 4/1, v / v) to afford the subject product 1.5 g, yield 49%.MS (ESI, m/z): 204(M +H)⁺.

References:

Shanghai Institute of Materia Medica, Chinese Academy of Sciences;JIANG, Hualiang;LIU, Hong;GENG, Meiyu;ZHENG, Mingyue;AI, Jing;WANG, Yulan;WU, Xiaowei;LI, Shuangjie;PENG, Xia;LI, Chunpu;CHEN, Kaixian;WANG, Bao EP3470415, 2019, A1 Location in patent:Paragraph 0098; 0099