4-Vinylpyridine → 2-(4-t-Butylphenyl)-7-(2-pyridin-4-yl-vinyl)-2,3-dihydro-isoindol-1-one

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Reaction Steps

7-Bromo-2-(4-t-butyl-phenyl)-2,3-dihydro-isoindol-1-one (0.14 g), 4-vinylpyridine (0.55 mL), Pd(OAc)2 (1.2 mg), tri-o-tolylphosphine (27.3 mg), and 2 mL of Et3N were added into a microwave reaction tube and subjected to 120° C., 10 min of microwave (2×). H2O and CHCl3 were added and the layers were separated. The aqueous phase was extracted with CHCl3 (3×). The combined organic phases were washed with H2O, dried over Na2SO4, filtered, then evaporated in vacuo to yield a light brown residue as crude product. The crude was purified by silica gel chromatography (25 g, 10-50% EtOAc/hexanes) to afford 2-(4-t-butylphenyl)-7-(2-pyridin-4-yl-vinyl)-2,3-dihydro-isoindol-1-one as an off-white solid:

Provenance & Evidence