108939-97-5

Usage

Molecular class

Organic compounds

Subclass

Tryptamines

Parent compound

1H-indole

Derivative groups

tert-Butyl group, dimethylsilyl group

Potential applications

Pharmaceutical development, precursor in organic synthesis

Effect of substituents

Can affect chemical and physical properties of the molecule

Upstream product

• 83-34-1 3-Methylindole 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 153942-69-9 3-bromo-1-(tert-butyl-dimethyl-silanyl)-1H-indole 
• 74-88-4 methyl iodide 

Downstream Products

• 83-34-1 3-Methylindole 
• 1432791-85-9 (1R,3aS,8bR)-dimethyl 1-(4-methoxyphenyl)-8b-methyl-1,3a,4,8b-tetrahydrocyclopenta[b]indole-3,3(2H)-dicarboxylate 
• 1432791-86-0 (1R,3aR,8bS)-dimethyl 1-(4-methoxyphenyl)-8b-methyl-1,3a,4,8b-tetrahydrocyclopenta[b]indole-3,3(2H)-dicarboxylate 
• 1432791-31-5 (1R,3aS,8bR)-dimethyl 4-(tert-butyldimethylsilyl)-1-(4-methoxy phenyl)-8b-methyl-1,3a,4,8b-tetrahydro cyclopenta[b]indole-3,3(2H)-dicarboxylate 
• 1432791-32-6 (1R,3aR,8bS)-dimethyl 4-(tert-butyldimethylsilyl)-1-(4-methoxy phenyl)-8b-methyl-1,3a,4,8b-tetrahydro cyclopenta[b]indole-3,3(2H)-dicarboxylate 

Relevant academic research and scientific papers

Preparation and Reactions of 1-(tert-Butyldimethylsilyl)-3-lithioindole. Regioselective Synthesis of 3-Substituted Indoles

1-(tert-Butyldimethylsilyl)-3-lithioindole (2) is prepared by metalation of the corresponding 3-bromo derivative 1 and efficiently reacts with electrophiles to give 3-substituted indoles 3 and 4.

Studies in the Protection of Pyrrole and Indole Derivatives

Treatment of pyrrole (1a), 2,5-dimethylpyrrole (1b), indole (3a), 2-methylindole (3b), 3-methylindole (3c), 2,3-dimethylindole (3d), 1,2,3,4-tetrahydro-9H-carbazole (5a), 5,6,7,8,9,10-hexahydrocycloheptindole (5b), and 6,7,8,9,10,11-hexahydro-5H-cyclo-octindole (5c) with sodium hydride in tetrahydrofuran, followed by phenyl t-butyl carbonate (8) gives the corresponding N-t-butoxycarbonyl (t-BOC) derivatives in satisfactory yields.By using chlorodimethyl-t-butylsilane instead of (8), N-dimethyl-t-butylsilyl derivatives are obtained, also in satisfactory yields.The use of the 2-(trimethylsilyl)ethoxycarbonyl (TEOC) group for the N-protection of the indole system, and the pivaloyloxymethyl (POM) group for the N-protection of the pyrrole and indole systems is also described.