4-CHLORO-5-AZAINDOLE Chemical Properties

Melting point:

189-192 °C(Solv: acetonitrile (75-05-8))

Boiling point:

335.8±22.0 °C(Predicted)

Density 

1.425±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly, Heated)

form 

powder

pka

14.30±0.40(Predicted)

color 

Yellow

InChI

InChI=1S/C7H5ClN2/c8-7-5-1-3-9-6(5)2-4-10-7/h1-4,9H

InChIKey

NGRAFQOJLPCUNE-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=CC2NC=CC1=2

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

25-41

Safety Statements 

26-45

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933998090

4-CHLORO-5-AZAINDOLE Usage And Synthesis

Uses

4-Chloro-1H-pyrrolo[3,2-c]pyridine is an intermediate used in the synthetic preparation of potent gp120-CD4 inhibitors.

Uses

4-CHLORO-5-AZAINDOLE is an intermediate used in the synthetic preparation of potent gp120-CD4 inhibitors.

Synthesis

General procedure for the synthesis of 4-chloropyrrolo[3,2-c]pyridine from 4-chloro-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine: 1. Synthesis of the intermediate 13-bromo-4-chloro-1H-pyrrolo[3,2-c]pyridine: To a solution of 4-chloro-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine (2.18 g, 14.2 mmol) in tetrahydrofuran (THF, 60 mL) was added manganese dioxide (MnO2, 7 g, 80.5 mmol) and the mixture was heated to reflux. After 5 hours of reaction, manganese dioxide (3 g, 34.5 mmol) was added and stirring was continued overnight. After completion of the reaction, the mixture was filtered through diatomaceous earth and the filtrate was concentrated to give a white solid product (1.95 g, 91% yield). 2. The indole derivative (1.48 g, 9.72 mmol) obtained above was dissolved in dichloromethane (CH2Cl2, 50 mL) and cooled to 0 °C under nitrogen protection. N-bromosuccinimide (NBS, 1.82 g, 10.2 mmol) was added slowly and the reaction was carried out for 30 min, then the ice bath was removed and stirring was continued for 30 min. After completion of the reaction, the target bromide (1.53 g, 68% yield) was filtered and dried under high vacuum. The product was detected by mass spectrometry (ES+), m/e = 231; 1H NMR (DMSO) δ 7.48 (1H, d), 7.80 (1H, s), 8.00 (1H, d).

References

[1] Patent: WO2007/95223, 2007, A2. Location in patent: Page/Page column 41

4-CHLORO-5-AZAINDOLE(60290-21-3)Related Product Information

• 3-bromo-4-chloro-1H-pyrrolo[3,2-c]pyridine
• (4-CHLORO-1-METHYL-1H-PYRROLO[3,2-C]PYRIDIN-3-YL)METHANOL
• 4-CHLORO-1-METHYL-1H-PYRROLO[3,2-C]PYRIDINE-3-CARBALDEHYDE
• 4,6-DICHLORO-1H-PYRROLO-[3,2-C]-PYRIDINE
• 4-CHLORO-5-AZAINDOLE
• 5-Azaindole
• Methyl 4,6-dichloro-5-azaindole-2-carboxylate
• 4-BROMO-7-CHLORO-3-IODO-5-AZAINDOLE
• 7-BROMO-4-CHLORO-5-AZAINDOLE-3-CARBOXYLIC ACID
• METHYL 4-CHLORO-5-AZAINDOLE-2-CARBOXYLATE
• 4-CHLORO-1-METHYL-1H-PYRROLO[3,2-C]PYRIDINE
• 4-BROMO-7-CHLORO-5-AZAINDOLE-3-CARBOXYLIC ACID
• 1-BENZYL-4-CHLORO-5-AZAINDOLE
• 7-BROMO-4-CHLORO-3-IODO-5-AZAINDOLE
• AURORA KA-5641
• AURORA KA-6631
• 4-CHLORO-7-BROMO-5-AZAINDOLE
• 4-BROMO-7-CHLORO-5-AZAINDOLE