N-bromobutanimide → HCID 53837501, compound

Participants

Reaction Steps

Step 3 A solution of tert-butyl 6-(4-fluorophenyl)-1H-indole-1-carboxylate (187.8 mg, 0.603 mmol) in THF (4 mL) was treated with N-bromosuccinimide (118 mg, 0.663 mmol) and stirred at rt. After 18 h, the solution was diluted with ether, washed with 2×10 mL aqueous sodium bisulfite (ca. 1.5 M), then with NaHCO3 (aq), dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from hexane to 90:10 hexane-EtOAc) provide tert-butyl 3-bromo-6-(4-fluorophenyl)-1H-indole-1-carboxylate as a white glassy foam (134 mg, 57%). 1H NMR (400 MHz, chloroform-d) δ 8.39 (1 H, br. s.), 7.59-7.68 (3 H, m), 7.54-7.59 (1 H, m), 7.48-7.53 (1 H, m), 7.14 (2 H, t, J=8.7 Hz), 1.67 (9 H, s).

Provenance & Evidence