Acide 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylique

Acide 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylique - Names and Identifiers

Name	4-chloro-1H-pyrrolo[3,2-e]pyridine-5-carboxylic acid
Synonyms	LogP T56 BM INJ FG GVQ 4-Chloro-7-azaindole-5-ca... 4-Chloro-7-azaindole-5-carboxylic acid 4-chloro-1H-pyrrolo[3,2-e]pyridine-5-carboxylic acid 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid 4-Chloro-1H-pyrrol[2,3-b] pyridine-5-carboxylic acid 1H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid, 4-chloro- Acide 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylique 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid, 5-Carboxy-4-chloro-1H-pyrrolo[2,3-b]pyridine
CAS	920966-03-6
InChI	InChI=1/C8H5ClN2O2/c9-6-4-1-2-10-7(4)11-3-5(6)8(12)13/h1-3H,(H,10,11)(H,12,13)

Acide 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylique - Physico-chemical Properties

Molecular Formula	C8H5ClN2O2
Molar Mass	196.59
Density	1.644±0.06 g/cm3(Predicted)
pKa	0.70±0.30(Predicted)
Storage Condition	Keep in dark place,Sealed in dry,Room Temperature
Refractive Index	1.744

Acide 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylique - Risk and Safety

Hazard Symbols	Xn - Harmful
Risk Codes	22 - Harmful if swallowed

Acide 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylique - Preparation solution concentration reference

	1mg	5mg	10mg
1 mM	5.087 ml	25.434 ml	50.867 ml
5 mM	1.017 ml	5.087 ml	10.173 ml
10 mM	0.509 ml	2.543 ml	5.087 ml
5 mM	0.102 ml	0.509 ml	1.017 ml

Last Update：2024-01-02 23:10:35

Acide 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylique - Reference Information

Application

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

preparation

step 1: synthesis of 4-chloro -1-(triisopropylsilyl)-7-azaindole at room temperature, 4-chloro -7 azaindole (100.00g,655.39mmol) is dissolved in DMF(1.2L), the ice bath was cooled to 0 ℃, NaH(39.47g,983.09mmol) was added in batches, after the addition, stirred at 0 ℃ for 1 hour, triisopropylchlorosilane (190.80g,983.09mmol, abbreviated TIPSCl) was added dropwise, and reacted at room temperature for 2 hours. Pour the reaction solution into 2L ice water, extract with petroleum ether (1L
x2), combine organic phases, wash with saturated salt water (1L x3), concentrate to dry under reduced pressure, and obtain 197.50g of colorless and transparent liquid by column chromatography (PE:EA = 1:0) with 97% yield. Step 2: Synthesis of 4-Chloro -1-(Triisopropylsilyl)-7-Azaindole -5-Ethyl formate Dissolve 4-Chloro -1-(Triisopropylsilyl)-7-Azaindole (20.00g,64.74mmol) in a four-mouth bottle of THF(100mL), cool to -75 ℃, add sec-butyl lithium (100mL,129.48mmol,Sec.BuLi) dropwise, after addition, stir at -75 ℃ for 1 hour, add chloroethyl chloroformate (17.80g,129.48mmol), after addition, react at -75 ℃ for 1 hour. Pour the reaction liquid into saturated ammonium chloride solution, separate the liquid, add ethyl acetate (100mL) to the aqueous phase for extraction, combine the organic phase, wash the saturated salt water, dry the anhydrous sodium sulfate, filter, concentrate, and pass through the column (PE:EA = 1:0~10:1) to obtain 23.15g of light yellow liquid with 94% yield. Step 3: Synthesis of 4-chloro-1H-pyrrolo [2,3-B] pyridine -5-carboxylic acid At room temperature, 4-chloro -1-(triisopropyl silicon)-7-azaindole -5-ethyl formate (12.94g,33.96mmol), ethanol (200mL) and 10% sodium hydroxide (100mL) are added to a single-mouth bottle, and the addition is completed, reaction at 60 ℃ for 2 hours. Evaporation under reduced pressure to remove ethanol, adjust the aqueous phase to pH = 4 with 1N dilute hydrochloric acid under ice bath, precipitate a large amount of white solid, filter, and dry the filter cake to obtain 8.60g of white solid with 77% yield.

Last Update：2024-04-09 15:16:36