Cesium carbonate → 3-(1-Hydroxyethyl)-4-(thiazol-5-yl)-1H-isochromen-1-one

Participants

Reaction Steps

4-Bromo-3-(1-hydroxyethyl)-1H-isochromen-1-one (Intermediate A2, 0.1 g, 0.372 mmol), 6-methyl-2-(thiazol-5-yl)-1,3,6,2-dioxazaborocane-4,8-dione (0.134 g, 0.56 mmol), Pd(PPh3)4 (0.021 g, 0.019 mmol) and Cs2CO3 (0.182 g, 0.56 mmol) in DMF (1 mL) were heated under microwave irradiation at 120° C. for 1 hrs and 15 min. Then, further 6-methyl-2-(thiazol-5-yl)-1,3,6,2-dioxazaborocane-4,8-dione (0.134 g, 0.56 mmol), Pd(PPh3)4 (0.021 g, 0.019 mmol) and Cs2CO3 (0.182 g, 0.56 mmol) were added and then resulting mixture was reacted for 5 hrs at 100° C. The crude product was purified via reverse phase chromatography with a Biotage C18 30 g SNAP column (Phase A, water 95%, ACN 4.9%, formic acid 0.1%; Phase B ACN 99.9%, formic acid 0.1%) to give the title compound (102 mg).

Provenance & Evidence