138344-46-4

Usage

Structure

An ester derivative of indole-1-carboxylic acid with a tert-butyl group

Usage

Synthetic intermediate used in the production of pharmaceuticals and agrochemicals

Physical form

White to off-white crystalline powder

Molecular weight

325.5 g/mol

Potential applications

Development of new drugs in the pharmaceutical industry and new pesticides or herbicides in the agricultural industry.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 28059-64-5 2-benzylaniline 
• 129822-44-2 (2-Benzyl-phenyl)-carbamic acid tert-butyl ester 

Downstream Products

• 129822-50-0 tert-butyl 3-phenyl-1H-indole-1-carboxylate 

Relevant academic research and scientific papers

Preparation of indoles and oxindoles from N-(tert-butoxycarbonyl)-2-alkylanilines

Treatment of dilithiated N-(tert-butoxycarbonyl)anilines 1 with dimethylformamide or carbon dioxide furnishes intermediates 3, 5, that are easily converted to N-(tert-butoxycarbonyl)indoles 4 and oxindoles (indol-2(3H)-ones, 7), respectively. Condensation of dilithiated 1 with N-methoxy-N-methylamides provides ketones 9 which are cyclized upon trifluoroacetic acid treatment to either 2-substituted 1-(tert-butoxycarbonyl)indoles 10 or 2-substituted indoles 11 depending on the reaction time. This general methodology has been applied to efficient synthesis of 1,2-alkyl-bridged indoles 12, 1,3,4,5-tetrahydrobenz[c,d]indole (16), 2a,3,4,5-tetrahydrobenz[c,d]indol-2(1H)-one (18), and 1-(tert-butoxycarbonyl)1H-pyrrolo[2,3-b]pyridine (21).