NCc1ccccc1.O=C1NCCc2cc(Br)ccc21>CC(=O)O.CC(=O)O.C[O-].Cc1ccccc1.[Na+].[Pd].c1ccc(P(CCP(c2ccccc2)c2ccccc2)c2ccccc2)cc1>O=C1NCCc2cc(NCc3ccccc3)ccc21In a small MW* sealed test tube was 6-bromo-3,4-dihydroisoquinolin-1(2H)-one (50 mg, 0.22 mmol), phenylmethanamine (24.16 µl, 0.22 mmol), palladium(II) acetate (2.483 mg, 0.01 mmol), Ethylenebis(diphenylphosphine) (8.81 mg, 0.02 mmol) and sodium methoxide (13.14 mg, 0.24 mmol) in toluene (2188 µl) combined to give a orange suspension. Heated reaction to 100°C overnight. Took LCMS - No reaction, only see unreacted SM. Discarded reaction.
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