Carbon tetrabromide → 5-Bromo-4-chloro-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

4-Chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyri dine (0.55 g, 1.78 mmol) was dissolved in THF (15 mL) and cooled to −78° C. s-BuLi (2.80 mL, 3.92 mmol) was then added dropwise. The solution was then stirred at −78° C. for 30 minutes. CBr4 (1.48 g, 4.45 mmol) was then added as a THF (2 mL) solution. The reaction was stirred for an additional 30 minutes as it was allowed to warm to 0° C. The reaction was then quenched with saturated NH4Cl and allowed to warm to room temperature. The reaction was then extracted with DCM (3×50 mL), dried, and filtered to give a crude residue. The crude residue was purified by chromatography with hexane to give 5-bromo-4-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (0.502 g, 72.7% yield).

Provenance & Evidence