Sodium Carbonate → HCID 58963165, compound

Participants

Reaction Conditions

Reaction Steps

Following the general procedure of Larock et al (Tetrahedron Lett, 1988, 29:4687), a mixture of methyl 2-(4-cyanophenylamino)-2-(4-(allyloxy)-3-bromo-5-ethylphenyl)acetate 4 (5.00 g, 11.7 mmol), Na2CO3 (3.09 g, 29.1 mmol), HCO2Na (800 mg, 11.7 mmol), Bu4N+C− (3.56 g, 12.8 mmol) and DMA was degassed by bubbling N2 for 1 h. Palladium(II) acetate (130 mg, 0.58 mmol) was added, the flask was sealed with a glass stopper and heated at 80° C. for 19 h. The mixture was poured into ½-saturated NH4Cl (500 mL) and extracted with diethylether (Et2O, 4×125 mL). The combined organic layers were washed with saturated NH4Cl (1×125 mL), water (1×125 mL), brine (1×125 mL), dried over magnesium sulfate (MgSO4), filtered, and concentrated. The residue was adsorbed onto Celite®, then purified by silica gel chromatography (SiO2, gradient elution 10–15–20% ethyl acetate/hexanes) to yield 1.11 g (27%) of methyl 2-(4-cyanophenylamino)-2-(7-ethyl-3-methylbenzofuran-5-yl)acetate 5 as a colorless solid.

Provenance & Evidence