89976-15-8

Usage

Purification Methods

Purify 7-iodoindole by chromatography through a silica gel column and eluting with CH2Cl2/hexane (1:3, v/v) followed by recrystallisation from hexane (colourless plates, m 55-56o). [Somei et al. Chem Pharm Bull Jpn 35 3146 1987, Somei & Saida Heterocycles 23 3114 1985.]

Upstream product

• 104682-96-4 2,3-dihydro-7-iodoindole 
• 187099-51-0 tert-butyl (2-iodo-6-((trimethylsilyl)ethynyl)phenyl)carbamate 
• 16078-30-1 1-Acetyl-2,3-dihydro-1H-indole 
• 104682-95-3 1-acetyl-2,3-dihydro-7-iodoindole 
• 187099-49-6 2-((trimethylsilyl)ethynyl)phenylaminocarboxylic acid tert-butyl ester 
• 615-36-1 2-bromoaniline 
• 161117-84-6 tert-butyl 2-iodophenylcarbamate 
• 78839-75-5 2-bromo-N-(tert-butoxycarbonyl)aniline 
• 615-43-0 2-iodophenylamine 
• 2861-59-8 N-formylindoline 
• 496-15-1 1-indoline 
• 910808-44-5 N-formyl-7-iodoindoline 

Downstream Products

• 114144-21-7 4-(indol-7-yl)-2-methyl-3-buten-2-ol 
• 104682-97-5 methyl 3-(indol-7-yl)acrylate 
• 123020-21-3 methyl 7-iodoindole-3-carboxylate 
• 473918-99-9 1-(2-benzyloxy-benzoyl)-7-iodo-1H-indole-3-carboxylic acid methyl ester 
• 473919-00-5 1'-(2-benzyloxy-benzoyl)-3-formyl-1'H-[4,7']biindolyl-1,3'-dicarboxylic acid 1-tert-butyl ester 3'-methyl ester 
• 1126143-98-3 (tetraethyl 4,4',4'',4'''-{[10-(2-(1H-indol-7-ylethynyl)-5-{[6-(1H-imidazol-1-yl)hexyl]oxy}phenyl)porphyrin-5,15-diyl-κN21,κN22,κN23,κN24]bis-[benzene-2,1,3-triylbis(oxy)]}tetrabutanoato(2-))zinc 
• 288371-43-7 (E)-3-(1H-indol-7-yl)acrylic acid 

Relevant academic research and scientific papers

Preparation of 7-halo-indoles by thallation of N-formylindoline and their attempted use for synthesis of the right-hand segment of chloropeptin

7-Substituted (Cl, Br, I) indoles were synthesized by using thallation of N-formylindoline as a key reaction. Two precursor tripeptides for the right-hand segment of chloropeptin were synthesized by using (R)-7′-iodo and 7′-bromotryptophans derived from each 7-substituted indole (I, Br) obtained by the above procedure.

A concise synthesis of 7-substituted indoles

7-Substituted indoles were synthesized by the basic cyclization of 6-substituted tert-butyl 2-(trimethylsilyiethynyl)phenylcarbamates which were derived by the lithiation of tert-butyl 2- (trimethylsilylethynyl)phenylcarbamate and the subsequent reaction with electrophiles.

The Chemistry of Indoles. XXXIX. A Facile Synthetic Method for 7-Substituted Indoles

A simple four-step synthetic method for 7-iodo-, 7-bromo- and 7-chloroindole was established with high overall yield starting from 2,3-dihydroindole.Several 7-substituted indoles carrying a carbon side chain and 7-methoxyindole were also synthetized.Keywords - thallation; 7-substituted indole; regioselective metalation; 7-iodoindole; 7-bromoindole; 7-chloroindole; 7-methoxyindole; methyl 3-(indol-7-yl)acrylate; 4-(indol-7-yl)-2-methyl-3-buten-2-ol; Heck reaction

SYNTHESIS OF 7-SUBSTITUTED INDOLES

A facile synthetic method for 7-iodoindole was established.Its versatility for the syntheses of 7-substituted indoles was shown by leading it to 7-methoxyindole and methyl 3-(indol-7-yl)acrylate.