5-Methoxy-3-indolecarboxylic acid Chemical Properties

Melting point:

172-175 °C

Boiling point:

447.6±25.0 °C(Predicted)

Density 

1.381±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

Crystalline

pka

3.95±0.30(Predicted)

color 

Red

CAS DataBase Reference

10242-01-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

HazardClass 

IRRITANT

HS Code 

2933998090

5-Methoxy-3-indolecarboxylic acid Usage And Synthesis

Uses

5-Methoxyindole-3-carboxylic Acid can be used in the synthesis of benzoheterocycle derivatives as vascular endothelial growth factor receptor-2 tyrosine kinase inhibitors and in the synthesis of indoleamine 2,3-dioxygenase 1 inhibitors with potential antitumor activity.

Synthesis

The general procedure for the synthesis of 5-methoxy-1H-indole-3-carboxylic acid from 5-methoxyindole and carbon dioxide was as follows: lithium tert-butoxide (LiOtBu, 160 mg, 2.00 mmol) and 5-methoxyindole (1a, 23.4 mg, 0.4 mmol) were added to a dry two-necked test tube. The reaction vessel was evacuated under high vacuum and the reaction atmosphere was replaced with a carbon dioxide balloon. Subsequently, N,N-dimethylformamide (DMF, 2 mL) was added and the mixture was stirred at 100 °C for 24 h of reaction. Upon completion of the reaction, the mixture was cooled to room temperature, the reaction was carefully quenched with 2N hydrochloric acid (HCl) solution and extracted with ethyl acetate (EtOAc, 5 times). The organic layers were combined, washed sequentially with water (2 times) and saturated brine (1 time) and dried over anhydrous magnesium sulfate (MgSO4). The dried organic phase was concentrated under reduced pressure and the residue was purified by preparative thin layer chromatography (TLC, unfolding reagent ratio of petroleum ether: acetone = 1:1) to afford the target product 5-methoxy-1H-indole-3-carboxylic acid (2a, 153.0 mg, 95% yield) as a white solid.

References

[1] Organic Letters, 2012, vol. 14, # 20, p. 5326 - 5329,4
[2] Heterocycles, 2015, vol. 90, # 2, p. 1196 - 1204

5-Methoxy-3-indolecarboxylic acid(10242-01-0)Related Product Information

• 4-Methoxybenzoic acid
• 4-Methoxyphenol
• (Trifluoromethoxy)benzene
• Indole-3-carboxylic acid
• p-Anisaldehyde
• Guaiacol
• Indole
• p-Anisidine
• 5-Methoxyindole
• Anisole
• Folic acid
• 5-METHYLINDOLE-2-CARBOXYLIC ACID
• 5-Norbornene-2-carboxylic acid
• 5-Methoxyindole-3-acetic acid
• Citric acid
• Ascoric Acid
• 5-Methoxy-2-indolecarboxylic acid
• Ethyl 5-acetyloxy-1,2-dimethylindole-3-carboxylate