Sodium Carbonate → HCID 23521672, compound

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Reaction Steps

A solution of N-(1-(4-bromophenyl)ethyl)-N-(ethanesulfonyl)pyrid-3-ylmethylamine (200 mg, 0.52 mmol), 2,4-difluorophenylboronic acid (124 mg, 0.78 mmol), sodium carbonate (0.78 ml of a 2M aqueous solution, 1.56 mmol), and tetrakis(triphenylphosphine)palladium(0) (26 mg, 0.023 mmol), under a nitrogen atmosphere was refluxed in dioxane (8 ml) for 6 h, then cooled to room temperature. The mixture was concentrated to a tan residue and resuspended in 2 ml dichloromethane. The suspension was subjected to purification by radial chromatography on a 2 micron silica plate eluting with 2 to 4% methanol/dichloromethane to afford the title compound. 1H NMR: 8.45 (bs,1H), 8.37 (bs,1H), 7.62 (d,1H,J=8 Hz), 7.45 (m,5H), 7.15 (m,1H), 6.95 (m,2H), 5.30 (q,1H,J=8 Hz), 4.35 (s,2H), 2.92 (q,2H,J=8 Hz), 1.67 (d,3H,J=8 Hz), 1.37 (t,3H,J=8 Hz). MS calcd. 416.5; MS (M+1) 417.1.

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