ChemicalBook CAS DataBase List 5-METHYLINDOLE-3-CARBOXYLIC ACID METHYL ESTER

5-METHYLINDOLE-3-CARBOXYLIC ACID METHYL ESTER synthesis

8synthesis methods

Product Name:5-METHYLINDOLE-3-CARBOXYLIC ACID METHYL ESTER
CAS Number:227960-12-5
Molecular formula:C11H11NO2
Molecular Weight:189.21

67-56-1 Synthesis

67-56-1
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10242-02-1
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$8.00/100mg

5-METHYLINDOLE-3-CARBOXYLIC ACID METHYL ESTER

227960-12-5
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$25.00/100mg

Yield: 90%

Reaction Conditions:

with thionyl chloride at 0 - 20; for 9 h;Reflux;

Steps:

For the derivativation of indole-3-carboxylic acids 2b and 2k
General procedure: Following the above procedure, the crude reaction mixture was diluted with MeOH and cooled to 0°C. Then SOCl2 (36 μL, 0.5 mmol) was added and stirred for 3 h at room temperature. Additional MeOH was added and the reaction mixture was heated to reflux for 6 h. The resulting mixture was quenched with H2O and extracted with EtOAc (3x). The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The resulting crude residue was purified by preparative TLC (hexane:EtOAc = 7:3) to afford the desired products 5a-b.

References:

Yoo, Woo-Jin;Nguyen, Thanh V. Q.;Guiteras Capdevila, Montse;Kobayashi, Shu [Heterocycles,2015,vol. 90,# 2,p. 1196 - 1204]