Sodium Carbonate → 2-(6,7-dichloro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-N-methyl-N-{2-(4-morpholinyl)-1-[3'-(1-piperidinylcarbonyl)-3-biphenylyl]ethyl}acetamide

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Reaction Steps

To a solution of N-[1-(3-bromophenyl)-2-(4-morpholinyl)ethyl]-2-(6,7-dichloro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-N-methylacetamide (75.0 mg, 0.13 mmol) and [3-(1-piperidinylcarbonyl)phenyl]boronic acid (35.0 mg, 0.15 mmol) in DMF (1.5 mL) was added Pd(dppf)Cl2 (5.5 mg, 0.0067 mmol) and a 2M aqueous solution of Na2CO3 (0.26 mL, 0.52 mmol). The resultant mixture was stirred at 80° C. for 16 h. The mixture was filtered through a 0.45 uM filter and was purified using a Gilson preparative HPLC (Xterra Prep RP, 30×100 mm, 45 mL/min, A: acetonitrile B: water, A: 30 to 70% over 10 min, PH 10 with NH4OH, UV detection at 214 nm) to give 65.4 mg (76%) of the title compound as off white solid. MS (ES) m/e 665.3 [M+H]+.

Provenance & Evidence