Sodium Chloride → 3-methyl-1-(2-phenoxyphenyl)-6,7-dihydro-2H-pyrrolo[3,4-c]pyridin-4(5H)-one

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Reaction Steps

A 2 mL microwave reaction vessel equipped with stirbar was charged with Example 92f (0.010 g, 0.044 mmol), 2-phenoxyphenylboronic acid (0.023 g, 0.109 mmol), 2 M aqueous sodium carbonate (0.218 mL, 0.437 mmol) and bis(triphenylphosphine)palladium(II) dichloride (3.06 mg, 4.37 μmol) in ethanol (0.200 mL)/DME (0.200 mL) and sealed. The mixture was heated at 120° C. for 30 minutes in a Biotage Initiator 2 monomode microwave reactor, then cooled to ambient temperature. The mixture was shaken in a separatory funnel with 75 mL ethyl acetate and 50 mL saturated aqueous sodium chloride. The organics were dried over anhydrous sodium sulfate. After filtration and solvent removal the residue was purified by reverse phase HPLC (C18, 0-100% CH3CN/water (0.1% TFA)) to afford the title compound (7.3 mg, 53%). 1H NMR (300 MHz, CD3OD) δ 10.74 (bds, 1H), 7.42 (dd, J=1.9, 7.6 Hz, 1H), 7.31-7.18 (m, 4H), 7.02-6.96 (m, 2H), 6.85 (m, 2H), 3.36 (m, 2H), 2.73 (m, 2H), 2.44 (s, 3H). MS (ESI+) m/z 319.2 (M+H)+.

Provenance & Evidence