Methyl iodide → 3-(2-Bromoethyl)-5-methoxy-1-methyl-1H-indole

Participants

Reaction Steps

A flask was charged with NaH (145 mg, 3.62 mmol), MeI (0.45 mL, 7.24 mmol) and THF (1.7 mL). The resulting grey suspension was stirred at rt for 5 min, then a solution of 3-(2-bromo-ethyl)-5-methoxy-1H-indole (230 mg, 0.90 mmol) in THF (4.1 mL) was added dropwise. After stirring for 18 h at rt, the reaction mixture was concentrated and purification by FC (hex/EtOAc 2:1, Rf=0.5) yielded the title compound as an yellow solid. LC-MS conditions 08Z acidic tR=0.93 min, [M+H]+=no ionization.

Provenance & Evidence