Cc1csc(N)n1.O=C1COCCN1c1cccc(Br)n1>CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd]>Cc1csc(Nc2cccc(N3CCOCC3=O)n2)n1**_September 16 2015_** 4-methylthiazol-2-amine (65 mg, 0.57 mmol), 4-(6-bromopyridin-2-yl)morpholin-3-one (146 mg, 0.57 mmol), 4-(6-bromopyridin-2-yl)morpholin-3-one (146 mg, 0.57 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (26.4 mg, 0.05 mmol) and cesium carbonate (223 mg, 0.68 mmol) in toluene (5 mL) were microwaved at 120 °C under N2 for one hour. LCMS showed no precursors and 68% of the desired mass MH+291 @ 0.87 min on a 2-min basic run. The reaction mixture was diluted with EtOAc, washed with water, filtered, and evaporated to give a brown solid as the crude product. **_September 17 2015_** The crude product was added to a Biotage column, and was eluted with 0-10% ammoniated MeOH in DCM. Collected fractions. Based on TLC and LCMS, the product fractions were combined, and evpoarated to give an orange-brown solid (150 mg). Based on LCMS, it was only 89% pure. The orange-brown solid was loaded on a Grace column, and eluted with 20-100%EtOAc in Heptane. Collected fractions. (Note: the solubility of the orange-brown solid was not good, and about 12 mL CH2Cl2 was used to dissolved everything) Based on TLC and LCMS, the product fractions were combined, and evpoarated to give an off-white solid (110 mg). Based on LCMS, it was 100% pure; based on M;R, it was > 95% pure.
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