1,10-Phenanthroline → 7-Methyl-5-(pyridin-4-ylmethoxy)-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one

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Reaction Steps

To a solution of 5-Iodo-7-methyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (100 mg, 0.22 mmol) in toluene (3 ml), pyridin-4-yl-methanol (26.4 mg, 0.24 mmol), copper(I) iodide (40 mg, 0.022 mmol), cesium carbonate (143 mg, 0.44 mmol), and 1,10-phenanthroline (7.9 mg, 0.044 mmol) were added. The resulting mixture was refluxed overnight, After cooling, the mixture was filtered through Celite® and concentrated. Column chromatography (80% EtOAc/Hexanes to 10% MeOH/EtOAc) provided the title compound as a yellow oil (44.3 mg, 47%). 1H NMR (300 MHz, CDCl3): δ 8.56 (br, 2H), 7.31-7.36 (m, 3H), 7.16-7.20 (m, 3H), 6.83 (s, 1H), 6.75 (s, 1H), 5.14 (s, 2H), 4.75 (s, 2H), 4.19 (s, 2H), 2.74 (s, 3H). GTPγS (0.0645).

Provenance & Evidence