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1H-Pyrrolo[2,3-b]pyridine-2-carboxaldehyde (9CI)

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1H-Pyrrolo[2,3-b]pyridine-2-carboxaldehyde (9CI) manufacturers

1H-Pyrrolo[2,3-b]pyridine-2-carboxaldehyde (9CI) Basic information
Application
Product Name:1H-Pyrrolo[2,3-b]pyridine-2-carboxaldehyde (9CI)
Synonyms:1H-Pyrrolo[2,3-b]pyridine-2-carboxaldehyde (9CI);1H-Pyrrolo[2,3-b]pyridine-2-carboxaldehyde;7-Azazindole-2-carboxyaldehyde;3-b]pyridine-2-carbaldehyde;7-Azaindole-2-carbaldehyde;7-azaindole-2-carboxaldehyde;1H-Pyrrolo[2,3-b]pyridin-2-carbaldehyd;2-aldehydeyl-7-azaindole
CAS:394223-03-1
MF:C8H6N2O
MW:146.15
EINECS:
Product Categories:PYRIDINE;ALDEHYDE
Mol File:394223-03-1.mol
1H-Pyrrolo[2,3-b]pyridine-2-carboxaldehyde (9CI) Structure
1H-Pyrrolo[2,3-b]pyridine-2-carboxaldehyde (9CI) Chemical Properties
density 1.368±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
pka11.93±0.40(Predicted)
AppearanceWhite to yellow Solid
InChIInChI=1S/C8H6N2O/c11-5-7-4-6-2-1-3-9-8(6)10-7/h1-5H,(H,9,10)
InChIKeyATTNRYFIYJHUOG-UHFFFAOYSA-N
SMILESC12NC(C=O)=CC1=CC=CN=2
CAS DataBase Reference394223-03-1
Safety Information
HS Code 2933998090
MSDS Information
1H-Pyrrolo[2,3-b]pyridine-2-carboxaldehyde (9CI) Usage And Synthesis
Application1H-pyrrolo[2,3-B]pyridine-2-carboxaldehyde is an important organic synthesis intermediate. Its aldehyde unit at position 2 exhibits high chemical reactivity and can be used for the structural modification and synthesis of various organic functional molecules. It has broad application potential in drug synthesis, biomedical research, and organic chemistry research.
Synthesis
1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, ethyl ester

221675-35-0

1H-Pyrrolo[2,3-b]pyridine-2-carboxaldehyde (9CI)

394223-03-1

Step c: Synthesis of 1H-pyrrolo[2,3-b]pyridine-2-carboxaldehyde [0452] A solution of ethyl 1H-pyrrolo[2,3-b]pyridine-2-carboxylate (190 mg, 1.0 mmol) in THF (5.0 mL) was slowly added dropwise at -20 °C to a suspension of LiAlH4 (42 mg, 1.1 mmol) in THF (10.0 mL) in a suspension of LiAlH4 (42 mg, 1.1 mmol). The reaction mixture was stirred continuously at -20 °C for 2 hours. Upon completion of the reaction, the reaction was quenched with saturated NH4Cl solution (10.0 mL). The reaction mixture was filtered and the filter cake was washed with ethyl acetate. The combined filtrates were sequentially washed with brine, dried over anhydrous Na2SO4 and then concentrated to afford 120 mg of 1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde in 67% yield. The resulting product was used directly in the next reaction without further purification.

References[1] Patent: WO2012/178015, 2012, A2. Location in patent: Page/Page column 113
Tag:1H-Pyrrolo[2,3-b]pyridine-2-carboxaldehyde (9CI)(394223-03-1) Related Product Information
N-(4-Chlorophenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxamide N-(4-Methoxyphenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxamide Methyl 5-cyano-1H-pyrrolo[2,3-b]pyridine-2-carboxylate Ethyl 4-methoxy-1H-pyrrolo[2,3-b]pyridine-2-carboxylate Morpholino[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]methanone N-(4-Chloro-2-methylphenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxamide 6-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid Methyl 3-bromo-6-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate Ethyl 6-chloro-7-azaindole-2-carboxylate 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, methyl ester 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, 6-(trifluoromethyl)-, methyl ester methyl 5-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, 4-chloro-, methyl ester 1H-Pyrrolo[2,3-b]pyridine-2-carboxaldehyde, 4-methoxy- 1H-Pyrrolo[2,3-b]pyridine-2-carboxaldehyde (9CI)