Methyl iodide → HCID 67085886, compound

Participants

Reaction Steps

To a solution of the product of step E (412 mg, 0.85 mmol) in DMF (10 mL) under a nitrogen atmosphere was added sodium hydride (60% dispersion in mineral oil, 69 mg, 1.70 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 1 h before addition of iodomethane (181 mg, 1.28 mmol). After stirring for an additional 2 h, the reaction mixture was quenched with water (50 mL) and extracted with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo to give tert-butyl 2-bromo-4-benzyloxy-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (420 mg, 99%) as a light-yellow solid: 1H NMR (CDCl3, 300 MHz) δ 7.31-7.50 (m, 5H), 7.21-7.27 (m, 1H), 6.75 (d, J=1.2 Hz, 1H), 5.05-5.23 (m, 3H), 4.67 (br s, 1H), 3.79 (s, 3H), 3.32 (br s, 1H), 2.42 (d, J=15.9 Hz, 1H), 2.21-2.36 (m, 1H), 2.07-2.21 (m, 1H), 1.85-1.96 (m, 1H), 1.55-1.65 (m, 1H), 1.39 (br s, 9H).

Provenance & Evidence