1H-Pyrrolo[2,3-b]pyridine, 5-bromo-1-(phenylsulfonyl)- Chemical Properties

storage temp. 

Sealed in dry,Room Temperature

Appearance

White to off-white Solid

Safety Information

WGK Germany 

3

1H-Pyrrolo[2,3-b]pyridine, 5-bromo-1-(phenylsulfonyl)- Usage And Synthesis

Synthesis

GENERAL STEPS: Sodium hydroxide (4.1 g, 102.8 mmol) was added to a dichloromethane solution containing tetrabutylammonium bromide (331 mg, 1.0 mmol) and 5-bromo-1H-pyrrolo[2,3-b]pyridine (6.7 g, 34.7 mmol). The mixture was stirred at 0 °C for 5 min. Subsequently, benzenesulfonyl chloride (5.7 mL, 44.5 mmol) was added slowly at 0 °C. The reaction mixture was continued to be stirred at 0 °C for 15 minutes, then gradually warmed to 25 °C and stirred continuously at this temperature for 12 hours. After completion of the reaction, the mixture was filtered and the filtrate was concentrated in vacuum and washed with hexane to afford 1-benzenesulfonyl-5-bromo-1H-pyrrolo[2,3-b]pyridine as a white solid (11.8 g, 100% yield). LC/MS analysis: m/e calculated value C13H10BrN2O2S [M+H]+ 338.20, measured values 337.1, 339.1 1H NMR (400 MHz, CDCl3) δ ppm: 6.56 (d, J = 4.0 Hz, 1H), 7.51 (m, 2H), 7.60 (m, 1H), 7.75 (d, J = 4.0 Hz, 1H), 7.98 (d, J = 2.1 Hz, 1H), 8.18 (m, 2H), 8.45 (d, J = 2.0 Hz. 1H).

References

[1] Patent: US2011/144105, 2011, A1. Location in patent: Page/Page column 16

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