Dichloromethane → HCID 68815060, compound

Participants

Reaction Steps

To a solution of 1-benzyl-5-bromo-3-methyl-2-phenyl-1H-indole (1.907 g, 5.068 mmol) in dioxane (51 ml) was added aqueous 2M K2CO3 (5.1 ml) followed by 4-methoxyphenylboronic acid (0.924 g, 6.082 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.083 g, 0.101 mmol). The mixture was stirred at RT for 0.75 hours, then warmed to ˜90° C. After heating for 18 hours, the reaction mixture was cooled and concentrated. The residue was partitioned between EtOAc (120 ml) and 1N HCl (30 ml). The layers were shaken, separated, and the organic layer washed with 1N HCl (2×20 ml) and brine (2×20 ml), dried over Na2SO4, filtered, concentrated, and dried to give a black residue (2.444 g). The residue was purified by flash column chromatography (silica), eluting with hexane, 0.5% and 1% EOAc/hexane, to give the product (1.223 g, 3.031 mmol, 60%) as an off-white solid, mp 117-122° C. 1H NMR (DMSO-d6) δ 2.26 (s, 3H), 3.79 (s, 3H), 5.32 (s, 2H), 6.85 (d, J=7.3 Hz, 2H), 7.00 (d, J=8.7 Hz, 2H), 7.15 (t, J=7.0 Hz, 1H), 7.20 (t, J=6.7 Hz, 2H), 7.35-7.44 (m, 5H), 7.49 (t, J=7.0 Hz, 2H), 7.62 (d, J=8.7 Hz, 2H), 7.75 (s, 1H); [ESI(+)], m/z 404 (M+H)+.

Provenance & Evidence