Dimethylformamide → HCID 21950054, compound

Participants

Reaction Steps

To a solution of 3-[1-(3-hydroxypropyl)-6-methoxy-1H-indol-3-yl]-4-(1-methyl-1H-indol-7-yl)-pyrrole-2,5-dione (3.0 g, 7.0 mmol) in solution of DMF (300 mL) was added PPh3 (2.6 g, 10.5 mmol) and CBr4 (3.3 g, 10.5 mmol). The reaction mixture was stirred at room temperature and under nitrogen for 1 h. The reaction was monitored by TLC and was completed after 2 h. The reaction mixture was diluted with EtOAc (300 mL) and water (800 mL). The aqueous phase was extracted with EtOAc (3×300 ml). The combined organic phases were washed with saturated aq NaHCO3 (300 mL), brine (500 mL) dried (MgSO4), filtered and concentrated. Flash chromatography (SiO2, 30% EtOAc/hexanes) gave the title compound (2.4 g, 71%) as a red solid. 1H NMR (300 MHz, DMSO-d6) 11.04 (s, 1H), 7.88 (s, 1H), 7.62 (d, J=6.1 Hz, 1H), 7.19 (d, J=2.6 Hz, 1H), 7.00–6.91 (m, 2H), 6.84 (d, J=6.0 Hz, 1H), 6.48 (d, J=2.5 Hz, 1H), 6.10 (m, 2H), 4.27 (t, J=5.8 Hz, 2H), 3.71 (s, 3H), 3.62 (s, 3H), 3.32 (t, J=5.8 Hz, 2H), 2.11 (m, 2H). MS (electrospray, m/z) 492.1/494.1 (M++1), 490.2/492.2 (M−−1).

Provenance & Evidence