1H-Pyrrolo[2,3-b]pyridine, 6-chloro-1-(phenylsulfonyl)-

1H-Pyrrolo[2,3-b]pyridine, 6-chloro-1-(phenylsulfonyl)- Property

Melting point:

136.4 °C

Boiling point:

488.6±48.0 °C(Predicted)

Density 

1.45±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

-0.78±0.30(Predicted)

Appearance

off-white solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

1H-Pyrrolo[2,3-b]pyridine, 6-chloro-1-(phenylsulfonyl)- Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 6-chloro-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine from benzenesulfonyl chloride was as follows: firstly, 6-chloro-7-azaindole (9.3 g, 61.1 mmol) was dissolved in 100 mL of anhydrous tetrahydrofuran (THF) under nitrogen protection. After the reaction mixture was cooled to 0°C, a dispersion of 60% sodium hydride (NaH) in mineral oil (3.5 g, 65.9 mmol) was added. After stirring for 1 h at room temperature, the mixture was again cooled to 0°C and benzenesulfonyl chloride (8.7 mL, 67.2 mmol) dissolved in 20 mL of anhydrous THF was added. The reaction mixture was continued to be stirred at room temperature for 1 hour. Subsequently, ethyl acetate was added to the mixture and the organic layer was washed three times with saturated sodium bicarbonate (NaHCO3) solution, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated. The resulting residue was purified by fast chromatography (ether/petroleum ether gradient elution from 1:4 to pure ether) to afford 1-benzenesulfonyl-6-chloro-1H-pyrrolo[2,3-b]pyridine (amorphous solid, 14.4 g, 80.7% yield). Thin layer chromatography (TLC) analysis showed an Rf value of 0.37 (ether/petroleum ether, 1/1). Liquid chromatography-mass spectrometry (LCMS) analysis: retention time (Rt) was 1.98 min and the molecular ion peak ([M + H]+) was 293.

References

[1] Patent: US2008/9514, 2008, A1. Location in patent: Page/Page column 21