ChemicalBook CAS DataBase List 1-METHYL-1H-INDOLE-5-CARBOXYLIC ACID

1-METHYL-1H-INDOLE-5-CARBOXYLIC ACID synthesis

9synthesis methods

Product Name:1-METHYL-1H-INDOLE-5-CARBOXYLIC ACID
CAS Number:186129-25-9
Molecular formula:C10H9NO2
Molecular Weight:175.18

1670-81-1 Synthesis

1670-81-1
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$6.00/250mg

74-88-4
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$15.00/10g

186129-25-9
101 suppliers
$22.00/100mg

Yield:186129-25-9 84%

Reaction Conditions:

Stage #1:1H-Indole-5-carboxylic acid with sodium hydride in N,N-dimethyl-formamide at 0; for 0.5 h;
Stage #2:methyl iodide in N,N-dimethyl-formamide at 20; for 12 h;

Steps:

5.2 General method for the synthesis of 1-alkyl-1H-indole-5-carbaldehyde (2, 3) and 1-alkyl-1H-indole-5-carboxylic acid derivatives (18a, 41)
General procedure: Indole-5-carboxaldehyde or indole-5-carboxylic acid (1 or 18, 1.0mmol) was dissolved in anhydrous DMF under magnetic stirring, and the temperature was set to 0°C. To this solution, 1.5mmol of NaH was added portionwise and the mixture was allowed to react for 30min. Then, 1.5mmol of alkyl iodide [methyl iodide or propyl iodide, or 4-[phenyl]iodomethylbenzene] in DMF was added dropwise and the reaction was warmed to room temperature and maintained under stirring for further 12h. Then, reaction was quenched by 10% aqueous solution of citric acid and washed with brine. Organic layer was separated, dried over anhydrous Na₂SO₄, filtered, and evaporated in vacuo. Crude products were purified by column chromatography using n-hexane/ethyl acetate (4:1 v:v) as mobile phase, to obtain intermediate compounds 2, 3, 18a and 41 with 89, 92, 90 and 78% of yields respectively.

References:

Ostacolo, Carmine;Di Sarno, Veronica;Lauro, Gianluigi;Pepe, Giacomo;Musella, Simona;Ciaglia, Tania;Vestuto, Vincenzo;Autore, Giuseppina;Bifulco, Giuseppe;Marzocco, Stefania;Campiglia, Pietro;Gomez-Monterrey, Isabel M.;Bertamino, Alessia [European Journal of Medicinal Chemistry,2019,vol. 167,p. 61 - 75]

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