Methyl iodide → tert-butyl 5-[1-(benzhydrylideneamino)ethyl]-4-chloro-1H-indole-1-carboxylate

Participants

Reaction Steps

To a stirred solution of 322 (1.22 g, 2.74 mmol) and iodomethane (0.17 mL, 2.74 mmol) in anhydrous THF (22.3 mL) at 0° C. was added dropwise a solution of potassium tert-butoxide (358.4 mg, 3.098 mmol) dissolved in THF (˜0.50 mL) over 5 min. The reaction mixture was stirred at RT under N2 for 3 h. The reaction mixture was diluted with EtOAc, and the organic layer was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo to afford 1.19 g (94.6%) of tert-butyl 5-[1-(benzhydrylideneamino)ethyl]-4-chloro-1H-indole-1-carboxylate (324) as a foam: MS (ESI) m/z=459.1 [M+1]+.

Provenance & Evidence