Cesium fluoride → 3-(5-methyl-2-thienyl)-1-(phenylmethyl)-2,5-dihydro-1H-pyrrole

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Reaction Conditions

Reaction Steps

The title compound can be prepared through a coupling palladium mediated reaction, e.g. starting from 2-bromo-5-methylthiophene and 1-(phenylmethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydro-1H-pyrrole. For example, to a solution of 2-bromo-5-methylthiophene (1.3 eq.) in THF, 1-(phenylmethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydro-1H-pyrrole (1 eq.), tetrakis(triphenylphosphine)palladium(0) (5% mol) and cesium fluoride (4 eq.) may be added at room temperature. The resulting mixture should be stirred at 80° C. for 1.5 hours. After cooling the solvent should be evaporated under reduced pressure and the residue partitioned between dichloromethane and sodium hydroxyde (1M). The organic phase should be evaporated under reduced pressure and the crude product purified by flash chromatography to give the title compound.

Provenance & Evidence