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

10242-02-1

5-METHYLINDOLE-3-CARBOXYLIC ACID METHYL ESTER

227960-12-5

GENERAL PROCEDURE: Following the above procedure, the crude reaction mixture was diluted with methanol (MeOH) and cooled to 0 °C. Sulfoxide chloride (SOCl2, 36 μL, 0.5 mmol) was then slowly added and the reaction was stirred at room temperature for 3 hours. Upon completion of the reaction, additional methanol (MeOH) was added and the reaction mixture was heated to reflux for 6 hours. At the end of the reaction, the reaction was quenched with deionized water (H2O) and extracted with ethyl acetate (EtOAc, 3 times). All organic layers were combined and dried with anhydrous magnesium sulfate (MgSO4) and subsequently concentrated under reduced pressure. Finally, the crude product was purified by preparative thin layer chromatography (TLC, unfolding reagent ratio petroleum ether: ethyl acetate = 7:3) to afford the target compounds, methyl 5-methylindole-3-carboxylate (5a-b).

67-56-1 Synthesis

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

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]