Potassium Carbonate → HCID 86704611, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl (2E)-3-(3-hydroxy-2-iodo-4-methoxyphenyl)prop-2-enoate (2.0 g, 5.99 mmol) in methanol (30 ml) was added trimethylboroxine (1.683 ml, 11.97 mmol), potassium carbonate (2.482 g, 17.96 mmol) and 1,1′-bis(di-tert-butylphosphino)ferrocene palladium dichloride (1.170 g, 1.796 mmol). The mixture was stirred overnight at 90° C. The solution was then filtered through a plug of silica gel (eluting with ethyl acetate), concentrated in vacuo and the residue was purified via column chromatography on a Biotage 65i column eluting with hexanes (1 CV) followed by a gradient of 0-50% ethyl acetate in hexanes (over 6.7 CVs) to furnish the desired compound. 1H NMR (CDCl3, 500 MHz) δ 7.95 (d, J=15.9 Hz, 1H), 7.14 (d, J=8.4 Hz, 1H), 6.74 (d, J=8.6 Hz, 1H), 6.27 (d, J=15.8 Hz, 1H), 3.91 (s, 3H), 3.80 (s, 3H), 2.34 (s, 3H).

Provenance & Evidence