Carbon tetrabromide → HCID 21949955, compound

Participants

Reaction Steps

To a solution of 3-[7-(3-hydroxypropyl)-1H-indol-3-yl]-4-(1-methyl-1H-indol-7-yl)pyrrole-2,5-dione (505 mg, 1.27 mmol) in 1:1 tetrahydrofuran/methylene chloride (60 mL) was added triphenylphosphine (330 mg, 1.25 mmol) followed by carbon tetrabromide (418 mg, 1.26 mmol). After one hour, additional triphenylphosphine (332 mg, 1.27 mmol) and carbon tetrabromide (414 mg, 1.25 mmol) was added. After 1 h, triphenylphosphine (330 mg, 1.26 mmol) and carbon tetrabromide (430 mg, 1.30 mmol) was added and stirred for 1 h. The reaction mixture was diluted with methylene chloride (100 mL), washed with saturated aq NaHCO3 (100 mL), brine (100 mL), dried (MgSO4) and concentrated. Flash chromatography (SiO2, 30% EtOAc/hexanes) gave the title compound (462 mg, 91%) as a red solid. 1H NMR (CDCl3) 8.93 (m, 1H), 8.66 (m, 1H), 8.07–7.87 (m, 4H), 6.64 (m, 1H), 6.49 (m, 2H), 3.72 (s, 3H), 3.41 (m, 2H), 2.96 (m, 2H), 2.21 (m, 2H). MS (electrospray, m/z) 464/462 (C24H20BrN3O2+H)+.

Provenance & Evidence