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Indole-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester

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Indole-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester Basic information
Product Name:Indole-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester
Synonyms:METHYL 1-BOC-1H-INDOLE-3-CARBOXYLATE;1H-Indole-1,3-dicarboxylic acid, 1-(1,1-diMethylethyl) 3-Methyl ester;1-tert-Butyl 3-Methyl 1H-indole-1,3-dicarboxylate;methyl 1-tert-butoxycarbonyl-1H-indole-3-carboxylate;tert-butyl methyl 1H-indole-1,3-dicarboxylate;Indole-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester
CAS:338760-26-2
MF:C15H17NO4
MW:275.3
EINECS:
Product Categories:
Mol File:338760-26-2.mol
Indole-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester Structure
Indole-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester Chemical Properties
Melting point 127.0 °C
Boiling point 387.3±34.0 °C(Predicted)
density 1.16±0.1 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
AppearanceWhite to off-white Solid
Safety Information
MSDS Information
Indole-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester Usage And Synthesis
Synthesis
Methyl indole-3-carboxylate

942-24-5

Di-tert-butyl dicarbonate

24424-99-5

INDOLE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 3-METHYL ESTER

338760-26-2

Methyl indole-3-carboxylate (17.1 mmol) was placed in a 50 mL round-bottomed flask, NaH (1.5 eq.) was added and cooled under ice bath conditions. THF (20 mL) was added slowly and stirred for 30 minutes. Subsequently, di-tert-butyl dicarbonate (1.5 eq.) was added and the reaction continued to stir overnight. Upon completion of the reaction, the reaction was quenched with saturated NaHCO3 solution, the reaction mixture was diluted with ether and washed with water. The organic layer was dried with anhydrous Na2SO4 and concentrated. The crude product was purified by column chromatography (ethyl acetate/hexane as eluent) to give 3-methyl-1H-indole-1,3-dicarboxylic acid-1-tert-butyl ester in 98% yield.

References[1] Patent: US2009/215828, 2009, A1. Location in patent: Page/Page column 13
[2] Patent: WO2009/103552, 2009, A1. Location in patent: Page/Page column 31
[3] Research on Chemical Intermediates, 2017, vol. 43, # 3, p. 1355 - 1363
[4] Tetrahedron, 2003, vol. 59, # 6, p. 747 - 754
[5] Chemistry - A European Journal, 2010, vol. 16, # 48, p. 14534 - 14544
Indole-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester Preparation Products And Raw materials
Raw materialsMethanol-->Methyl indole-3-carboxylate-->Di-tert-butyl dicarbonate-->tert-Butyl 3-formyl-1H-indole-1-carboxylate-->Tetrahydrofuran-->Sodium hydride
Preparation Products2,3-Dihydro-1H-indole-3-carboxylic acid methyl ester
Tag:Indole-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester(338760-26-2) Related Product Information
Indole Indole-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester tert-Butyl 3-formyl-1H-indole-1-carboxylate Methyl 1-Boc-1H-pyrrole-3-carboxylate 1-(tert-Butoxycarbonyl)-1H-indole-3-carboxylic acid 3-Hydroxymethylindole-1-carboxylic acid tert-butyl ester