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12th March 2013 @ 05:12

Arylation of AT-6 with 4-sulfamoylphenyl boronic acid pinacol ester, under the conditions described in AT-7-1.

To a degassed solution of isopropanol (1 mL) and potassium carbonate (1 M, 0.173 mL, 0.173 mmol, 2.0 equiv.) was added AT-6 (0.020 g, 0.087 mmol, 1.0 equiv.) and 4-sulfamoylphenyl boronic acid pinacol ester (0.030 g, 0.10 mmol, 1.2 equiv.) and the reaction mixture degassed for a further 5 minutes. PdCl2dppf (0.012 g, 0.017 mmol, 0.2 equiv.) was added and the reaction mixture stirred at 80 C overnight. 

Not quite to plan

The balloon used to degas the reaction mixture contained traces of acid(?), likely to be from the previous reaction using POCl3, which contaminated the reaction mixture. The reaction mixture showed a complex mixture of products after stirring overnight at 80 C. 

 

HIRAC

AT-10-1.pdf
Attached Files
AT-10-1.pdf
AT-10-1.jpg