C1COCCN1.CCOC(=O)c1cncc(Br)c1>C1COCCO1.CC(C)(C)[O-].CN(C)c1ccccc1-c1ccccc1P(C1CCCCC1)C1CCCCC1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[Pd]>CCOC(=O)c1cncc(N2CCOCC2)c1
ethyl 5-bromonicotinate (200 mg, 0.87 mmol), morpholine (0.083 mL, 0.96 mmol), sodium 2-methylpropan-2-olate (167 mg, 1.74 mmol), 2'-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (17.11 mg, 0.04 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (19.90 mg, 0.02 mmol) were suspended in dioxane (5 mL) and sealed into a microwave tube. The reaction was heated to 100 °C for 1 hour in the microwave reactor and cooled to RT. LCMS analysis appeared to indicate addition of 2 morpholine rings and the reaction was abandoned.
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