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

pka

11.93±0.40(Predicted)

Appearance

White to yellow Solid

InChI

InChI=1S/C8H6N2O/c11-5-7-4-6-2-1-3-9-8(6)10-7/h1-5H,(H,9,10)

InChIKey

ATTNRYFIYJHUOG-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

394223-03-1

Safety Information

HS Code 

2933998090

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

Application

1H-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

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

1H-Pyrrolo[2,3-b]pyridine-2-carboxaldehyde (9CI)(394223-03-1)Related Product Information

• 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, methyl ester
• ETHYL 6-CHLORO-7-AZAINDOLE-2-CARBOXYLATE
• 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, 6-(trifluoromethyl)-, methyl ester
• ETHYL 4-METHOXY-1H-PYRROLO[2,3-B]PYRIDINE-2-CARBOXYLATE
• 6-(TRIFLUOROMETHYL)-1H-PYRROLO[2,3-B]PYRIDINE-2-CARBOXYLIC ACID
• METHYL 3-BROMO-6-(TRIFLUOROMETHYL)-1H-PYRROLO[2,3-B]PYRIDINE-2-CARBOXYLATE
• N-(4-METHOXYPHENYL)-1-(PHENYLSULFONYL)-1H-PYRROLO[2,3-B]PYRIDINE-2-CARBOXAMIDE
• methyl 5-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate
• 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, 4-chloro-, methyl ester
• METHYL 5-CYANO-1H-PYRROLO[2,3-B]PYRIDINE-2-CARBOXYLATE
• 1H-Pyrrolo[2,3-b]pyridine-2-carboxaldehyde, 4-methoxy-
• N-(4-CHLOROPHENYL)-1-(PHENYLSULFONYL)-1H-PYRROLO[2,3-B]PYRIDINE-2-CARBOXAMIDE
• 1H-PYRROLO[2,3-B]PYRIDINE-2-CARBOXYLIC ACID
• MORPHOLINO[1-(PHENYLSULFONYL)-1H-PYRROLO[2,3-B]PYRIDIN-2-YL]METHANONE
• 1H-Pyrrolo[2,3-b]pyridine-2-carboxaldehyde (9CI)
• N-(4-CHLORO-2-METHYLPHENYL)-1-(PHENYLSULFONYL)-1H-PYRROLO[2,3-B]PYRIDINE-2-CARBOXAMIDE