2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → Ethyl 6-chloro-7-(4-(8-methylquinolin-2-ylcarbamoyl)phenoxy)chroman-4-carboxylate

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To a solution of ethyl 7-(4-carbamoylphenoxy)-6-chlorochroman-4-carboxylate (0.025 g, 0.0665 mmol), 2-chloro-8-methylquinoline (0.0130 g, 0.0732 mmol), X-PHOS (0.0238 g, 0.0732 mmol), and dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.00634 g, 0.0133 mmol) in THF (0.6 ml) was added tris(dibenzylideneacetone)dipalladium (0.0030 g, 0.0033 mmol), and the reaction was heated to 60° C. for 16 hours. The reaction was loaded directly onto silica gel and eluted with a gradient of 5-70% EtOAc/hexanes to yield the desired compound (0.024 g, 0.0464 mmol, 69.8% yield).

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