Methyl iodide → HCID 67086028, compound

Participants

Reaction Steps

Sodium hydride (38 mg, 0.950 mmol) was added to a solution of the product of step A (240 mg, 0.636 mol) in DMF (4 mL) at room temperature under N2. After 1 h, methyl iodide (134 mg, 0.058 mL, 0.943 mol) was added, and the reaction allowed to proceed for an additional 1 h. The mixture was quenched with H2O, upon which a solid precipitated out of solution. The solids were filtered off to provide tert-butyl 3-bromo-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (248 mg, 100%) as a brown solid: 1H NMR (300 MHz, CDCl3) δ 7.40 (s, 1H), 7.35 (d, J=8.5 Hz, 1H), 7.19 (d, J=8.5 Hz, 1H), 5.30-5.10 (br m, 1H), 4.76-4.56 (br m, 1H), 3.54 (s, 3H), 3.49-3.19 (br m, 1H), 2.46 (d, J=16.0 Hz, 1H), 2.37-2.08 (m, 2H), 1.97-1.86 (m, 1H), 1.69-1.57 (m, 1H), 1.50 (s, 9H).

Provenance & Evidence