ethyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate Chemical Properties

Boiling point:

406.0±40.0 °C(Predicted)

Density 

1.391±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

11.76±0.40(Predicted)

Appearance

Light yellow to light brown Solid

Safety Information

HazardClass 

IRRITANT

ethyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate Usage And Synthesis

Application

Ethyl 5-chloro-6-azaindole-2-carboxylate is an organic synthesis intermediate and a pharmaceutical intermediate that can be used in laboratory research and development processes as well as in chemical and pharmaceutical research and development.

Synthesis

Step 2: Synthesis of ethyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate 10-b To a solution of 3-(2-chloro-5-nitropyridin-4-yl)-2-oxopropanoic acid ethyl ester 10-a (2.726 g, 10 mmol) in THF (80 mL) and EtOH (30 mL) was added a saturated ammonium chloride solution (50 mL). Subsequently, iron powder (2.747 g, 4.9 eq.) was added in batches at room temperature under vigorous stirring, and then the mixture was heated to reflux for 2 hours. Upon completion of the reaction, the mixture was cooled to room temperature, filtered through diatomaceous earth and washed with warm THF/ethanol (1:1, v/v). The filtrate was evaporated and the residue was dissolved in 100 mL of water with stirring and refluxing. The resulting precipitate was thermally filtered, washed twice with warm water and then dried under vacuum to give ethyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate 10-b (1.9 g, 84% yield). m/z = 225 (M + H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm: 1.36 (t, J = 6.8 Hz, 3H), 4.39 (q, J = 6.7 Hz, 2H), 7.15 (s, 1H), 7.76 (s, 1H), 8.64 (s, 1H), 12.59 (br s, 1H).

References

[1] Patent: WO2012/80450, 2012, A1. Location in patent: Page/Page column 24
[2] Molecules, 2014, vol. 19, # 9, p. 13342 - 13357
[3] Patent: WO2006/59164, 2006, A2. Location in patent: Page/Page column 20
[4] Patent: WO2006/67532, 2006, A1. Location in patent: Page/Page column 19
[5] Patent: US2008/125459, 2008, A1. Location in patent: Page/Page column 9

ethyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate(800401-67-6)Related Product Information

• 5-Chloro-1H-pyrazolo[3,4-b]pyridine
• 5-Chloro-1H-pyrazolo[4,3-b]pyridine
• 1-(5-Bromo-7-azaindole)ethanone
• Ethanone, 1-(1H-pyrrolo[2,3-c]pyridin-3-yl)- (9CI)
• ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate
• 4-BroMo-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile
• 5-AZAINDOLE-2-CARBOXYLIC ACID
• 3-Cyano-4-azaindole
• 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile
• 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, 5-chloro-
• 1H-PYRROLO[3,2-C]PYRIDINE-2-CARBOXYLIC ACID ETHYL ESTER
• ethyl 5-chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylate
• 1H-Pyrrolo[2,3-b]pyridine, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
• 1H-PYRROLO[3,2-B]PYRIDINE-2-CARBOXYLIC ACID
• 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid
• ethyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate
• 5-CHLORO-1H-PYRROLO[2,3-C]PYRIDINE
• 1H-PYRROLO[2,3-C]PYRIDINE-2-CARBALDEHYDE