77435-11-1

Basic information

• Product Name: 1H-Indole-3-carboxylic acid, 2-methyl-1-(phenylmethyl)-, ethyl ester
• CAS NO: 77435-11-1
• Molecular Formula: C19H19NO2
• Molecular Weight: 293.365
• Mol File: 77435-11-1.mol

Chemical Properties

• CAS DataBase Reference: 1H-Indole-3-carboxylic acid, 2-methyl-1-(phenylmethyl)-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-3-carboxylic acid, 2-methyl-1-(phenylmethyl)-, ethyl ester(77435-11-1)
• EPA Substance Registry System: 1H-Indole-3-carboxylic acid, 2-methyl-1-(phenylmethyl)-, ethyl ester(77435-11-1)

Safety Data

• Hazardous Substances Data: 77435-11-1(Hazardous Substances Data)

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 104014-46-2 1-<2-(Benzylamino)phenyl>ethanon 
• 95-20-5 2-methyl-1H-indole 
• 17901-58-5 1-benzyl-2-methyl-1H-indole 
• 541-41-3 chloroformic acid ethyl ester 
• 100-39-0 benzyl bromide 

Downstream Products

• 53855-47-3 ethyl 2-methyl-1H-indole-3-carboxylate 
• 77435-28-0 3-hydroxymethyl-2-methylindoline 
• 6872-06-6 2-methyl indoline 

Relevant articles and documents

Me2AlCl-mediated carboxylation, ethoxycarbonylation, and carbamoylation of indoles

Various 1-methyl-, 1-triisopropylsilyl-, and 1-benzylindoles are carboxylated under CO2 pressure (3.0 MPa) with the aid of 1.0 molar equiv of Me2AlCl to give 1-substituted indole-3-carboxylic acids in good to excellent yields. Mechanistic studies suggest that the intermediate, an indol-3-ylaluminum ate complex, was reversibly formed by electrophilic addition of Me2AlCl to the substrate followed by deprotonation of the resulting adduct. This method is successfully extended to alkoxycarbonylation with ethyl chloroformate and carbamoylation with naphthalen-1-yl isocyanate, which afford ethyl indole-3-carboxylates and N-naphthalen-1-ylindole-3-carboxamides, respectively.

Synthesis of substituted indole from 2-aminobenzaldehyde through [1,2]-aryl shift

A mild, efficient, and simple method for the synthesis of 3-ethoxycarbonylindoles has been developed. Addition of ethyl diazoacetate (EDA) to 2-aminobenzaldehydes cleanly affords the indole core. As opposed to other common approaches for the synthesis of indole, this method displays both excellent functional group tolerance and perfect regiochemical control. This allowed the synthesis of a variety of useful indole building blocks from 2-aminobenzaldehydes derived from readily available anthranilic acids.

INDOLE-3-CARBOXYLIC ACID AMIDE, ESTER, THIOAMIDE AND THIOL ESTER COMPOUNDS BEARING ARYL OR HETEROARYL GROUPS HAVING SPHINGOSINE-1-PHOSPHATE (S1P) RECEPTOR ANTAGONIST BIOLOGICAL ACTIVITY

The invention provides compounds represented by the formula I, each of which compounds may have sphingosine-1-phosphate receptor agonist and or antagonist biological activity: and wherein the variables Y, R4, n, A, X, Z, R1, o, Rsup