Acrylamide → ethyl 6-[(1E)-3-amino-3-oxoprop-1-enyl]-8-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

To the mixture of 0.4 g (1.0 mmol) of ethyl 6-Bromo-8-Chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate, 45 mg (0.2 mmol) of palladium acetate, 122 mg (0.4 mmol) of tri-o-tolylphosphine, 451 mg (5.5 mmol) of sodium acetate under nitrogen atmosphere was added 6 mL of anhydrous dimethylformamide, followed by addition of 107 mg (1.5 mmol) of acrylamide. The resulting mixture was shaken at 110° C. for 85 hrs. LC-MS indicated that the reaction was done. To the reaction was added 50 mL of ethylacetate. The resulting organic solution was washed with brine and dried over anhydrous magnesium sulfate. After removing the volatiles, the residue was purified by reverse phase chromatography to afford 0.23 g off-white solid, which was carried on to the next step.

Provenance & Evidence