1-(Benzenesulfonyl)-3-bromo-1H-pyrrolo[2,3-b]pyridine

1-(Benzenesulfonyl)-3-bromo-1H-pyrrolo[2,3-b]pyridine Property

Melting point:

140-145 °C

Boiling point:

511.4±53.0 °C(Predicted)

Density 

1?+-.0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

0.12±0.30(Predicted)

Safety

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26

WGK Germany 

3

HS Code 

2933399990

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.

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.

P405Store locked up.

1-(Benzenesulfonyl)-3-bromo-1H-pyrrolo[2,3-b]pyridine Chemical Properties,Usage,Production

Synthesis

Under nitrogen protection, 3-bromo-1H-pyrrolo[2,3-b]pyridine (175 mg, 0.89 mmol), tetrabutylammonium bromide (10 mg, 0.03 mmol), finely ground sodium hydroxide (107 mg, 2.67 mmol), and dichloromethane (5 mL) were added to a dry round-bottomed flask, and mixed by stirring. The reaction mixture was cooled to 0 °C in an ice bath, followed by slow dropwise addition of benzenesulfonyl chloride (0.142 mL, 1.11 mmol). After the dropwise addition, the reaction mixture was gradually warmed up to room temperature and stirred continuously at this temperature for 1 hour. Upon completion of the reaction, the reaction was quenched by the addition of water (6 mL) and extracted twice with dichloromethane. The organic layers were combined, washed sequentially with water and saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure to give an orange solid crude product. The crude product was ground in pentane, filtered, washed with pentane and dried to give 294 mg of the target compound 3-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine in 98% yield. The product was characterized by 1H NMR (300 MHz, CDCl3) with the following chemical shift δ (ppm): 8.48 (dd, J = 1.5, 4.8 Hz, 1H), 8.24-8.17 (m, 2H), 7.82 (dd, J = 1.5, 8.0 Hz, 1H), 7.79 (s, 1H), 7.60 (dd, J = 7.5 Hz. 1H), 7.54-7.46 (m, 2H), 7.27 (dd, J = 4.8, 8.0 Hz, 1H).

References

[1] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 701 - 719
[2] Patent: US2006/100218, 2006, A1. Location in patent: Page/Page column 52
[3] Patent: US2011/15173, 2011, A1. Location in patent: Page/Page column 30
[4] Patent: US2011/257187, 2011, A1. Location in patent: Page/Page column 21-22
[5] Patent: US2011/257189, 2011, A1. Location in patent: Page/Page column 35