7-Azaindole-5-carboxaldehyde Chemical Properties

Melting point:

181-182°C

Density 

1.368±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

solid

pka

13.02±0.40(Predicted)

Appearance

Light yellow to yellow Solid

InChI

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

InChIKey

HDANOCTXZFZIHB-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933399990

7-Azaindole-5-carboxaldehyde Usage And Synthesis

Synthesis

The general procedure for the synthesis of 7-azaindole-5-carbaldehyde from N,N-dimethylformamide and 5-bromo-7-azaindole was as follows: to an anhydrous THF solution (50 mL) of 5-bromo-1H-pyrrolo[2,3-b]pyridine (1.0 g, 5.0 mmol, 1.0 eq.) was slowly added, under protection of argon, at -78 °C a hexane solution of 1.6 M n-butyllithium (6.7 mL, 10.7 mmol, 2.1 eq.). The reaction mixture was stirred at -78 °C for 40 min. Subsequently, 1 mL of anhydrous DMF was added to the resulting suspension and the reaction mixture was continued to be stirred overnight at room temperature. Upon completion of the reaction, the reaction mixture was quenched with saturated NH4Cl solution. The organic layer was separated and the aqueous phase was extracted with EtOAc. The organic layers were combined, washed with brine, dried over Na2SO4, filtered and concentrated to afford 1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (Intermediate 3a) as a yellow solid (1.0 g; yield: 69%; UPLC purity: 98%).

References

[1] Patent: US2018/179199, 2018, A1. Location in patent: Paragraph 0459-0460
[2] Patent: WO2016/114816, 2016, A1. Location in patent: Paragraph 0300

7-Azaindole-5-carboxaldehyde(849067-90-9)Related Product Information

• 4-HYDROXY-7-AZAINDOLE