| Identification | Back Directory | [Name]
1H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid, 4-chloro- | [CAS]
920966-03-6 | [Synonyms]
4-Chloro-7-azaindole-5-ca...
4-Chloro-7-azaindole-5-carboxylic acid
4-Chloro-7-azaindole-5-carboxylicacid95%
4-Chloro-7-azaindole-5-carboxylic acid 95%
4-Chloro-1H-pyrrol[2,3-b] pyridine-5-carboxylic acid
1H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid, 4-chloro-
4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid 95%
4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid, 5-Carboxy-4-chloro-1H-pyrrolo[2,3-b]pyridine | [Molecular Formula]
C8H5ClN2O2
| [MDL Number]
MFCD10574983
| [MOL File]
920966-03-6.mol | [Molecular Weight]
196.59 |
| Chemical Properties | Back Directory | [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 Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302 | [Precautionary statements ]
P280-P305+P351+P338 | [Hazard Codes ]
Xn | [Risk Statements ]
22 | [WGK Germany ]
WGK 3 | [HS Code ]
2933998090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Questions And Answer | Back Directory | [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. |
| Hazard Information | Back Directory | [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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