Reacción #495358

Ecuación de reacción

TBAF

s-BuLi

4-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

I2

ammonium chloride

sodium sulfite

→

4-chloro-5-iodo-1H-pyrrolo[2,3-b]pyridine

Rendimiento 73.1%

Disolventes

ethyl acetate

water

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction was stirred at −78° C. for 20 minutes
2. 2
   Extracciónthe mixture was extracted with hexanes (200 mL)
3. 3
   Lavadowashed with brine
4. 4
   Secadodried over sodium sulfate
5. 5
   OtroAfter removal of the solvent
6. 6
   workup.DISSOLUTIONthe residue was dissolved in THF (50 mL)
7. 7
   workup.STIRRINGThe reaction was stirred at room temperature for 10 minutes
8. 8
   OtroThe organic layer was separated
9. 9
   Lavadowashed with brine
10. 10
    Secadodried over sodium sulfate
11. 11
    OtroAfter removal of the solvent
12. 12
    workup.STIRRINGstirred for 10 minutes
13. 13
    OtroThe solid formed
14. 14
    Filtraciónwas collected by filtration

Procedimiento

s-BuLi (59.3 mL, 71.2 mmol, 1.4M in cyclohexane) at −78° C. was added to 4-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (10.0 g, 32.4 mmol) in THF (100 mL), and the reaction was stirred at −78° C. for 30 minutes. I2 (20.5 g, 80.9 mmol) in THF (50 mL) was added, and the reaction was stirred at −78° C. for 20 minutes. A saturated ammonium chloride solution (50 mL) and a saturated sodium sulfite solution (50 mL) were added, and the mixture was extracted with hexanes (200 mL), washed with brine and dried over sodium sulfate. After removal of the solvent, the residue was dissolved in THF (50 mL), and TBAF (32.4 mL, 32.4 mmol) was added. The reaction was stirred at room temperature for 10 minutes, and then water (20 mL) and ethyl acetate (100 mL) were added. The organic layer was separated, washed with brine, and dried over sodium sulfate. After removal of the solvent, the residue was suspended in dichloromethane (“DCM”; 20 mL) and stirred for 10 minutes. The solid formed was collected by filtration to give 4-chloro-5-iodo-1H-pyrrolo[2,3-b]pyridine (6.6 g, 73% yield) as a solid.

Fuente