Methyl iodide → HCID 57501702, compound

Participants

Reaction Steps

Add NaH (0.83 g, 20.8 mmol) to a solution of 1-(6-nitro-1H-indol-3-yl)-2-pyrrolidin-1-yl-ethane-1,2-dione (5.0 g, 17.42 mmol) in THF (60 mL). Stir at room temperature for 10 min, add iodomethane (1.18 mL, 19.2 mmol), and continue stirring for 18 h. Dilute with water and extract with EtOAc (2×). Filter the solid that formed between the layers during the extraction. Dry organic portion, concentrate, and combine the solids. Triturate the solid with ether, filter, and dry to obtain the title compound (5.20 g, 99%). 1H NMR (400 MHz, DMSO-d6): δ 8.59 (m, 2H), 8.30 (d, 1H, J=8.8 Hz), 8.17 (dd, 1H, J=8.8, 2.2 Hz), 4.01 (s, 3H), 3.48 (t, 2H, J=6.8 Hz), 3.41 (t, 2H, J=6.4 Hz), 1.85 (m, 4H).

Provenance & Evidence