4,6-Dichloro-1H-indole-2-carboxylic acid Chemical Properties

Melting point:

238-239 °C

Boiling point:

476.9±40.0 °C(Predicted)

Density 

1.663±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO (Slightly, Methanol (Slightly, Heated)

form 

Solid

pka

4.10±0.30(Predicted)

color 

Pale Beige

CAS DataBase Reference

101861-63-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

4,6-Dichloro-1H-indole-2-carboxylic acid Usage And Synthesis

Uses

MDL 29951 is an allosteric inhibitor of the enzyme fructose 1,6-bisphosphatase.

Synthesis

The general procedure for the synthesis of 4,6-dichloroindole-2-carboxylic acid from ethyl 4,6-dichloroindole-2-carboxylate was as follows: first, the intermediate 4,6-dichloro-1H-indole-2-carboxylic acid (I-id) was prepared. This was done as follows: ethyl 4,6-dichloro-1H-indole-2-carboxylate (1c) (50 g, 193.72 mmol) was dissolved in a mixed solvent consisting of THF and water (1:1, 900 mL), followed by the addition of LiOH-H2O (24.41 g, 581.7 mmol). The reaction mixture was stirred at room temperature for 18 hours. Upon completion of the reaction, THF was removed by distillation, the residue was diluted with water (400 mL) and acidified with aqueous 2N HCl to pH 6.0. The acidified solution was extracted with ethyl acetate (4×150 mL), and the combined organic layers were washed with brine (350 mL), dried over anhydrous Na2SO4, and finally concentrated under reduced pressure to afford 4,6-dichloro-1H-indole-2 -carboxylic acid (1d) 39 g in 87.5% yield as a light brown solid. The product was characterized by 1H NMR (400 MHz, DMSO-d6) and ESI MS: 1H NMR δ 12.25 (s, 1H), 7.43 (s, 1H), 7.25 (s, 1H), 7.05 (s, 1H); ESI MS m/z 227.7 (M-H).

References

[1] Patent: WO2014/37900, 2014, A1. Location in patent: Paragraph 27; 28
[2] Gazzetta Chimica Italiana, 1958, vol. 88, p. 1147,1153, 1159
[3] Journal of Medicinal Chemistry, 1990, vol. 33, # 11, p. 2944 - 2946

4,6-Dichloro-1H-indole-2-carboxylic acid(101861-63-6)Related Product Information

• Indole-2-carboxylic acid
• Dichloroacetic acid
• 2,3,4-Trihydroxybenzoic acid
• Folic acid
• 2,4-Dichlorobenzoic acid
• Indole-3-butyric acid
• Indole-3-acetic acid
• Indometacin
• Indole
• Citric acid
• Ascoric Acid
• 4,6-DICHLORO-1H-INDOLE-2-CARBOXYLIC ACID ETHYL ESTER
• 5,7-DICHLORO-1H-INDOLE-2-CARBOXYLIC ACID ETHYL ESTER
• 4,6-Dichloro-1H-indole
• 4,6-DICHLORO-3-[(1E)-3-OXO-3-(PHENYLAMINO)-1-PROPENYL]-1H-INDOLE-2-CARBOXYLIC ACID SODIUM SALT
• ETHYL 4,6-DICHLORO-3-FORMYL-1H-INDOLE-2-CARBOXYLATE
• ALPHA-PHENYL-1-(2-PHENYLETHYL)-4-PIPERIDINEMETHANOL
• ETHYL 3-(2-CARBOXY-VINYL)-4,6-DICHLORO-1H-INDOLE-2-CARBOXYLATE