Reacción #57233

Ecuación de reacción

4-bromo-2-iodo-1-phenylsulfonyl-1H-pyrrolo[2,3-b]pyridine

3-formylbenzeneboronic acid

sodium bicarbonate

→

title compound

Rendimiento 77.0%

4-Bromo-2-(3-formylphenyl)-1-phenylsulfonyl-1H-pyrrolo[2,3-b]pyridine

Rendimiento 77.0%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was purged with nitrogen
2. 2
   Otrocapped
3. 3
   TemperaturaAfter cooling to room temperature the reaction
4. 4
   Concentraciónwas concentrated under vacuum
5. 5
   Lavadowashed with water, brine
6. 6
   Secadodried over sodium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Otroevaporated to dryness under vacuum
9. 9
   OtroPurification by flash chromatography by silica gel (0-4% ethyl acetate in methylene chloride)

Procedimiento

In a sealed pressure tube was added 4-bromo-2-iodo-1-phenylsulfonyl-1H-pyrrolo[2,3-b]pyridine (2.1 mmol; preparation disclosed in WO03/000690A1), 3-formylbenzeneboronic acid (2.1 mmol), N,N-dimethylformamide (15 mL), aqueous saturated sodium bicarbonate (5 mL) and tetrakis(triphenylphosphine)palladium(0) (0.1 mmol). The reaction was purged with nitrogen, capped and stirred at 100° C. for 16 h. After cooling to room temperature the reaction was concentrated under vacuum, taken up in ethyl acetate, washed with water, brine, dried over sodium sulfate, filtered and evaporated to dryness under vacuum. Purification by flash chromatography by silica gel (0-4% ethyl acetate in methylene chloride) gave the title compound as a white solid (77%). ESMS [M+H]+: 441.2

Fuente