Methanol → 6-(5-(Methylsulfonyl)-1,3,4-thiadiazol-2-yl)isoquinoline

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Reaction Steps

To a 25 mL round bottom flask was added 6-(5-(methylthio)-1,3,4-thiadiazol-2-yl)isoquinoline (0.28 g, 1.1 mmol), Oxone® monopersulfate (2.7 g, 4.3 mmol) and 10 mL of MeOH. The reaction mixture was heated at reflux for 4 hours. Sodium thiosulfate solution (25 mL, 1 M) was added to the mixture. The mixture was then extracted with EtOAc (3×30 mL). The combined organic layers were concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with a gradient of 0 to 90% EtOAc in hexanes) to provide 6-(5-(methylsulfonyl)-1,3,4-thiadiazol-2-yl)isoquinoline (0.19 g, 60%) as a yellow solid. LCMS (M+H) 292 calc. for C12H10N3O2S2 292.0. 1H NMR (400 MHz, CD3OD): δ ppm 2.77-2.79 (m, 3H), 7.19 (d, J=5.67 Hz, 1H), 7.49-7.53 (m, 1H), 7.54-7.58 (m, 1H), 7.78 (d, J=5.87 Hz, 1H), 7.92 (s, 1H), 8.57 (s, 1H).

Provenance & Evidence