ChemicalBook CAS DataBase List METHYL 7-METHOXY-1H-INDOLE-2-CARBOXYLATE

METHYL 7-METHOXY-1H-INDOLE-2-CARBOXYLATE synthesis

4synthesis methods

Product Name:METHYL 7-METHOXY-1H-INDOLE-2-CARBOXYLATE
CAS Number:84638-71-1
Molecular formula:C11H11NO3
Molecular Weight:205.21

2-Propenoic acid, 3-(2-amino-3-methoxyphenyl)-2-bromo-, methyl ester, (2Z)-

1586740-64-8
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METHYL 7-METHOXY-1H-INDOLE-2-CARBOXYLATE

84638-71-1
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Yield:84638-71-1 86%

Reaction Conditions:

with 1,4-diaza-bicyclo[2.2.2]octane;copper(l) iodide;potassium carbonate in 1,4-dioxane; for 4 h;Schlenk technique;Inert atmosphere;Reflux;

Steps:

General Procedure forthe CuI Catalyzed Intramolecule Coupling Reaction Using 3-(2-Aminophenyl)-2-Bromo-acrylates (2a-2t):

General procedure: A dried 50 mL Schlenk tubeequipped with a rubber septum and magnetic stir bar was charged with3-(2-aminophenyl)-2-bromoacrylate (128 mg, 0.5 mmol), K₂CO₃(345 mg, 2.5 mmol), CuI (9.5 mg, 0.05 mmol), DABCO (0.1 mmol) and dioxane (4mL). The mixture was degassed 3 times under N₂ atmosphere thenheated at reflux until the starting material was consumed as indicated by TLC.The cooled mixture was partitioned between 20 mL of water and 20 mL of ethylacetate. The organic layer was separated, and the aqueous layer was extractedwith ethyl acetate (10 mL x 2). The combined organic layers were dried (Na₂SO₄)and concentrated. The residue was purified by flash chromatography on silicagel eluted with petroleum/ethylacetate to provide corresponding 2-carboxyindole.

References:

Xiao, Xiong;Chen, Tian-Qi;Ren, Jiangmeng;Chen, Wei-Dong;Zeng, Bu-Bing [Tetrahedron Letters,2014,vol. 55,# 13,p. 2056 - 2060] Location in patent:supporting information