Sodium Carbonate → HCID 131735936, compound

Participants

Reaction Conditions

Reaction Steps

3-(3-Bromo-phenyl)-N-methoxy-N-methylacrylamide (14.5 g, 53.7 mmol) prepared in Step 1, 4-(methylthio)phenylboronic acid (18.0 g, 107.4 mmol), Pd(PPh3)4 (3.1 g, 2.7 mmol) and sodium carbonate (17.1 g, 161.1 mmol) were added to a mixed solvent of N,N-dimethylformamide (100.0 mL) and distilled water (10.0 mL). The reaction mixture was stirred at 80° C. for 20 hours, quenched with a saturated solution of ammonium chloride, and then extracted with diethyl ether three times. The combined extract was washed with brine, 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=1/3) to give 17.6 g of the titled compound as a yellow solid.

Provenance & Evidence