5-Chloro-7-azaindole Chemical Properties

Melting point:

161-162°C

Density 

1.425±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

12.97±0.40(Predicted)

form 

Powder

color 

White to pale brown

InChI

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

InChIKey

MFZQJIKENSPRSJ-UHFFFAOYSA-N

SMILES

C12NC=CC1=CC(Cl)=CN=2

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

Safety Statements 

24/25

RIDADR 

UN2811

WGK Germany 

3

HazardClass 

6.1

HazardClass 

IRRITANT

HS Code 

29339900

5-Chloro-7-azaindole Usage And Synthesis

Chemical Properties

Yellow powder

Uses

5-Chloro-7-azaindole can be used as an organic synthesis intermediate and a pharmaceutical intermediate, and is mainly used in laboratory research and development processes and chemical and pharmaceutical production processes.

Synthesis

Step 3: Synthesis of 5-chloro-7-azaindole (Ib) Under nitrogen protection, 25.0 g of 4-(2-amino-5-chloropyridin-3-yl)-2-methylbut-3-yn-2-ol, 120 mL of N-methylpyrrolidone, and 130 mL of water were added to a 500 mL double jacketed reactor. The mixture was heated to 75-80 °C (jacket temperature about 95 °C) and a vacuum of 350 mbar was applied at about 100 °C. Subsequently, 85 mL of 28% sodium hydroxide aqueous solution was slowly added dropwise over 30-45 minutes at 75-80°C. Upon completion of the dropwise addition, the dropping funnel was rinsed with 5 mL of water and the mixture was stirred at 78-81 °C overnight. The jacket temperature and vacuum need to be adjusted during stirring to maintain a steady distillate flow rate. Under typical laboratory conditions, 50 mL of the water/acetone mixture can be distilled in approximately 2 hours. Continuous water replenishment is required during the reaction to keep the reaction volume constant at about 270 mL. After the reaction is complete, the mixture is cooled to 50-55 °C and 60 mL of toluene is added. The two-phase mixture was stirred at 50-55 °C for 15-30 min, followed by standing for 15-30 min to separate the layers. After separating the aqueous layer, the aqueous layer was extracted with 3 x 50 mL of toluene at 50-55°C. The toluene layers were combined and washed with 5 x 40 mL of water at 50-55°C. The toluene layer was concentrated to dryness and the residue (17.3 g) was recrystallized with 90 mL of toluene to give 13.0 g (71% yield) of 5-chloro-7-azaindole (Ib) as light yellow crystals with an HPLC purity of 96.7% (% area).

References

[1] Patent: US2011/28511, 2011, A1. Location in patent: Page/Page column 14

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