Diisopropylethylamine → 1H-Pyrrolo[2,3-b]pyridine, 6-bromo-1-[tris(1-methylethyl)silyl]-

Participants

Reaction Conditions

Reaction Steps

6-bromo-1H-pyrrolo[2,3-b]pyridine (587, 275 mg, 1.39 mmol) was dissolved in 4 mL of dry dioxane. DIEA (3 equiv) and TIPS-OTf (2.5 equiv) were added and the reaction was stirred at 50° C. overnight. The reaction was then diluted with 20 mL of ethyl acetate and washed 2 times with 10 mL NaHCO3 (aq., 5%) and once with 10 mL brine. The organic fraction was dried over MgSO4, evaporated and diluted with 5.5 mL of dry toluene (˜10 mg bromide per 0.2 mL of solution) to use directly in the next reaction step.

Provenance & Evidence