1H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid, 4-chloro- Chemical Properties

Density 

1.644±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

solid

pka

0.70±0.30(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C8H5ClN2O2/c9-6-4-1-2-10-7(4)11-3-5(6)8(12)13/h1-3H,(H,10,11)(H,12,13)

InChIKey

SJZMFAGWKZNYPX-UHFFFAOYSA-N

SMILES

C12NC=CC1=C(Cl)C(C(O)=O)=CN=2

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2933998090

1H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid, 4-chloro- Usage And Synthesis

Application

4-Chloro-1H-pyrrolo[2,3-B]pyridine-5-carboxylic acid is an organic intermediate that can be prepared from 4-chloro-7-azaindole via a three-step reaction. It has been reported in the literature to be used to prepare the compound (S)-4-(3-(2,2,2-trifluoroethylcarbamoyl)piperidin-1-amino)-1H-7-azaindole-5-carboxamide, which is a JAK family inhibitor.

Synthesis

General procedure for the synthesis of 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid from ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate: to a solution of 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid ethyl ester (10.5 g, 46.7 mmol) in ethanol (84 mL), was added an aqueous 1 M sodium hydroxide solution ( 140 mL, 140 mmol) and the reaction mixture was stirred at 60 °C for 1.5 hours. Upon completion of the reaction, the mixture was cooled to 4 °C and acidified with 1 M aqueous hydrochloric acid to pH < 7. The precipitated solid was collected by filtration and washed with deionized water to afford 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (9.0 g, 98% yield). The structure of the product was confirmed by 1H-NMR (DMSO-d6) δ: 6.62-6.64 (1H, m), 7.67-7.70 (1H, m), 8.71 (1H, s), 12.32 (1H, br s), 13.22 (1H, br s) and mass spectra (ESI) m/z: 195 (M-H)-.

References

[1] Chemical and Pharmaceutical Bulletin, 2015, vol. 63, # 5, p. 341 - 353
[2] Patent: WO2007/7919, 2007, A2. Location in patent: Page/Page column 45

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