N-bromobutanimide → HCID 68486193, compound

Participants

Reaction Steps

NBS (0.137 g, 0.771 mmol) was added to ethyl 5-[(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)oxy]-1H-indole-2-carboxylate (0.255 g, 0.701 mmol) dissolved in DMF (2 mL) and the resulting mixture was stirred overnight at RT. The reaction mixture was partitioned between EtOAc and water. The organic layer was separated, dried over MgSO4, filtered and the solvent evaporated. Purification was accomplished by silica gel column chromatography (0 to 50% EtOAc/hexanes) to afford the title compound (0.121 g, 39%) as an oily solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.90 (br. s., 1H), 7.27 (d, 1H), 7.02-7.07 (m, 1H), 7.01 (s, 1H), 4.43 (q, 2H), 4.11 (t, 2H), 4.00 (t, 2H), 1.43 (t, 3H), 0.91 (s, 9H), 0.11 (d, 6H). LC-MS (ES+) m/z 442.2 [M+H].

Provenance & Evidence