Sodium Carbonate → N-methoxy-N-methyl-3-(3'-methylsulfanyl-biphenyl-4-yl)-acrylamide

Participants

Reaction Conditions

Reaction Steps

3-(4-Bromo-phenyl)-N-methoxy-N-methyl-acrylamide (11.7 g, 43.2 mmol) prepared in Step 1 of Preparation 1, 3-(methylthio)phenylboronic acid (14.5 g, 86.4 mmol), Pd(PPh3)4 (2.5 g, 2.2 mmol) and sodium carbonate (13.7 g, 129.6 mmol) were added to a mixed solvent of N,N-dimethylformamide (200.0 mL) and distilled water (50.0 mL). The reaction mixture was stirred at 80° C. for 7 hours and then extracted with ethyl acetate. The extract was washed with a saturated solution of ammonium chloride, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5) to give 17.0 g of the titled compound as a yellow solid.

Provenance & Evidence