Ethyl 4,6-dichloro-1H-indole-2-carboxylate Chemical Properties

Melting point:

171-172

Boiling point:

405.0±40.0 °C(Predicted)

Density 

1.432±0.06 g/cm3(Predicted)

storage temp. 

2-8°C, protect from light

pka

13.21±0.30(Predicted)

Appearance

White to off-white Solid

CAS DataBase Reference

53995-82-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2933998090

Ethyl 4,6-dichloro-1H-indole-2-carboxylate Usage And Synthesis

Uses

Ethyl 4,6-dichloro-1H-indole-2-carboxylate is used as a pharmaceutical intermediate in pharmaceutical synthesis and scientific research.

Synthesis

Step 3: Preparation of the intermediate ethyl 4,6-dichloro-1H-indole-2-carboxylate (I-ic) Ethyl 2-[2-(3,5-dichlorophenyl)hydrazin-1-ylidene]propanoate (26 g, 94.50 mmol in two batches) was reacted with polyphosphoric acid (260 g, each batch) at 110 °C with stirring for 3 hours. Upon completion of the reaction, the reaction mixture was slowly poured into crushed ice, stirred thoroughly and the precipitate was collected by filtration. The resulting solid was alkalized with saturated aqueous NaHCO3 (adjusted pH to 10) and subsequently extracted with ethyl acetate (3 x 150 mL). The organic layers were combined, washed with brine, dried over anhydrous Na2SO4 and concentrated. The crude product was purified by silica gel column chromatography using a hexane solution of 30% ethyl acetate as eluent to afford ethyl 4,6-dichloro-1H-indole-2-carboxylate (I-ic) 36 g in 73.8% yield as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.46 (s, 1H), 7.46 (s, 1H), 7.30 (s, 1H), 7.12 (s, 1H), 4.36 (q, J = 7.2 Hz, 2H), 1.35 (t, J = 7.2 Hz, 3H). ESI MS: m/z 255.8 (M-H).

References

[1] Patent: WO2006/109633, 2006, A1. Location in patent: Page/Page column 182-183
[2] Organic Process Research and Development, 2000, vol. 4, # 6, p. 477 - 487
[3] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 4, p. 326 - 330
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 2011, vol. 54, # 10, p. 645 - 656
[5] ACS Infectious Diseases, 2017, vol. 3, # 3, p. 225 - 236

Ethyl 4,6-dichloro-1H-indole-2-carboxylate(53995-82-7)Related Product Information

• Indole
• Ethyl cyanoacetate
• RESMETHRIN
• Ethyl propiolate
• Ethyl formate
• ISOXADIFEN-ETHYL
• Urethane
• Triethyl orthoformate
• Ethyl cyanoformate
• Ethyl acetate
• Ethanol
• Ethyl acrylate
• Benzocaine
• Trinexapac-ethyl
• Ethylparaben
• Ethyl chloroformate
• 4,6-Dichloro-1H-indole
• 4,6-Dichloro-1H-indole-2-carboxylic acid