1,4-Dioxane → 1H-Pyrrolo[2,3-b]pyridine, 6-bromo-1-[tris(1-methylethyl)silyl]-

Participants

Reaction Conditions

Reaction Steps

In a 25 mL round-bottomed flask, 6-bromo-1H-pyrrolo[2,3-b]pyridine (250 mg, 1.27 mmol, Eq: 1.00), TIPS-OTf (972 mg, 860 μl, 3.17 mmol, Eq: 2.5) and DIEA (492 mg, 665 μl, 3.81 mmol, Eq: 3) were combined with dioxane (6.25 ml) to give a light brown solution. The reaction mixture was heated to 55° C. and stirred for 16 h. The reaction mixture was poured into 20 mL EtOAc and extracted with sat NaHCO3 (3×10 mL). The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 12 g, 5% to 10% EtOAc in hexanes) to give 6-bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (380 mg, 85%) of colorless oil.

Provenance & Evidence