Methyl iodide → HCID 67273994, compound

Participants

Reaction Steps

To a slurry of sodium hydride (60% in mineral oil, 0.575 g, 14 mmol) in DMF (40 mL) was added in portions 7-(2-methoxy-ethoxy)-1H-indole (Cuny, Gregory D.; Yuan, Junying; Jagtap, Prakash; Degterev, Alexei. US 2005119260, 2.5 g, 13 mmol) over 5 minutes at 5-10° C. The reaction mixture was stirred at rt for 1 h until hydrogen evolution ceased, and methyl iodide (3.7 g, 26 mmol) was added dropwise over 5 minutes at 10-20° C. The mixture was stirred at rt for 2 h, quenched with ice/water, and extracted with tert-butylmethyl ether. The organics were washed, dried and concentrated. The residue was crystallized from ether/hexane to yield the desired compound (2.28 g) as a yellowish liquid. MS (ISP): m/e 206.3 (M+H)+

Provenance & Evidence