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18th March 2013 @ 08:34
Microwave-assisted arylation of AT-6.   A solution of AT-6 (0.020 g, 0.87 mmol, 1.0 equiv.), 4-(dimethylamido)phenyl boronic acid pinacol ester(0.029 g, 0.10 mmol, 1.2 equiv.) and PdCl2dppf (0.013 g, 0.018 mmol, 0.2 equiv.) in isopropanol (2 mL) and K2CO3 (1 M, 0.17 mL, 0.17 mmol, 2.0 equiv.) was heated to 80 C in a microwave reactor (200 W) for 30 minutes.  The reaction mixture was cooled, diluted with methanol (10 mL) and filtered through Celite. The reaction mixture was concentrated under reduced pressure. The residue was purified by flash column chromatography (95:45:0.5 dichloromethane:methanol:ammonia) to give the product as a brown solid (0.023 g, 88%). Some starting material was observed; the reaction may need a little longer in the microwave (45 minutes?). Maybe we should get our own microwave...  NMR [data]5931[/data] 1H NMR [data]6398[/data] 13C{1H} NMR    HIRAC [data]5926[/data]
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