5-Bromo-1-methyl-1H-indole → HCID 71284599, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-1-methyl-1H-indole (9.8 g, 46.7 mmol) in THF (40 mL) was added n-BuLi (2.5M in hexanes, 22.3 mL, 55.8 mmol, 1.2 eq) at −78° C. dropwise over 15 min. The mixture was stirred for 30 min at −78° C. before a solution of N-methoxy-N-methylbutyramide (7.35 g, 56.0 mmol, 1.2 eq) in THF (10 mL) was added. After stirred at −78° C. for 10 min, the reaction was quenched with saturated aqueous NH4Cl. The resulting mixture was extracted by ether (3×30 mL) and combined organic layers were dried over Na2SO4. The crude product was purified by flash chromatography (0-10% EtOAc in hexanes) to give the title compound (5.40 g, 26.8 mmol, 57%) as a white solid.

Provenance & Evidence