![](/CAS/GIF/186129-25-9.gif)
1-METHYL-1H-INDOLE-5-CARBOXYLIC ACID synthesis
- Product Name:1-METHYL-1H-INDOLE-5-CARBOXYLIC ACID
- CAS Number:186129-25-9
- Molecular formula:C10H9NO2
- Molecular Weight:175.18
![Indole-5-carboxylic acid](/CAS/GIF/1670-81-1.gif)
1670-81-1
336 suppliers
$6.00/250mg
![Iodomethane](/CAS/GIF/74-88-4.gif)
74-88-4
340 suppliers
$15.00/10g
![1-METHYL-1H-INDOLE-5-CARBOXYLIC ACID](/CAS/GIF/186129-25-9.gif)
186129-25-9
98 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]
![Methyl 1-Methyl-1H-indole-5-carboxylate](/CAS/GIF/128742-76-7.gif)
128742-76-7
44 suppliers
$109.00/1g
![1-METHYL-1H-INDOLE-5-CARBOXYLIC ACID](/CAS/GIF/186129-25-9.gif)
186129-25-9
98 suppliers
$22.00/100mg
![5-Bromo-1-methyl-1H-indole](/CAS/GIF/10075-52-2.gif)
10075-52-2
116 suppliers
$45.00/1 g
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124-38-9
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$175.00/23402
![1-METHYL-1H-INDOLE-5-CARBOXYLIC ACID](/CAS/GIF/186129-25-9.gif)
186129-25-9
98 suppliers
$22.00/100mg
![5-Bromo-1-methyl-1H-indole](/CAS/GIF/10075-52-2.gif)
10075-52-2
116 suppliers
$45.00/1 g
![MONOMETHYL CARBONATE SODIUM SALT](/CAS/GIF/6482-39-9.gif)
6482-39-9
9 suppliers
inquiry
![1-METHYL-1H-INDOLE-5-CARBOXYLIC ACID](/CAS/GIF/186129-25-9.gif)
186129-25-9
98 suppliers
$22.00/100mg
![Methyl indole-5-carboxylate](/CAS/GIF/1011-65-0.gif)
1011-65-0
272 suppliers
$6.00/250mg
![1-METHYL-1H-INDOLE-5-CARBOXYLIC ACID](/CAS/GIF/186129-25-9.gif)
186129-25-9
98 suppliers
$22.00/100mg