6-ETHOXYCARBONYLINDOLE-2-CARBOXYLIC ACID ETHYL ESTER Chemical Properties

Melting point:

119-121℃

Boiling point:

420.2±25.0 °C(Predicted)

Density 

1.240±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

13.84±0.30(Predicted)

Appearance

Light yellow to yellow Solid

6-ETHOXYCARBONYLINDOLE-2-CARBOXYLIC ACID ETHYL ESTER Usage And Synthesis

Uses

6-Ethoxycarbonylindole-2-carboxylic acid ethyl ester is utilized in medicinal chemistry for the design and development of new drugs.

Synthesis

Synthesis of diethyl 1H-indole-2,6-dicarboxylate (3): ethyl 4-(3-ethoxy-2,3-dioxopropyl)-3-nitrobenzoate (2) (8.5 g, 27.5 mmol) was suspended in acetic acid (75 mL) and heated to 75°C. After the solid was completely dissolved, water (56 mL) was slowly added, followed by activated zinc powder (17.9 g, 27.5 mmol). 27.5 mmol). The reaction temperature was maintained at 80°C with continuous stirring for 2 hours. Upon completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate (50 mL) and filtered through a diatomaceous earth pad. The filtrate was washed sequentially with water (2 x 100 mL), saturated sodium bicarbonate solution (2 x 100 mL) and brine (100 mL). The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford the yellow solid product 3 (6.0 g, 83% yield).1H NMR (500 MHz, DMSO-d6) δ 1.33 (m, 6H), 4.34 (m, 4H), 7.21 (s, 1H), 7.65 (d, J = 8.5 Hz, 1H), 7.75 (d, J = 8.5 Hz, 1H), 7.12 (s, 1H), 7.12 (s, 1H), 8.12 (s, 1H). 8.12 (s, 1H), 12.25 (s, 1H). Mass spectrum (MS) m/z (M-H): 259.9.

References

[1] Patent: WO2014/149164, 2014, A1. Location in patent: Paragraph 00802; 00826
[2] Organic and Biomolecular Chemistry, 2015, vol. 13, # 9, p. 2588 - 2599
[3] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 3, p. 938 - 941
[4] Patent: US2006/276453, 2006, A1. Location in patent: Page/Page column 32-33
[5] Patent: WO2011/71716, 2011, A1. Location in patent: Page/Page column 40-41

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