Ethanol → 6-(5-(Methylthio)-1,3,4-thiadiazol-2-yl)benzo[d]isothiazole

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Reaction Conditions

Reaction Steps

To a stirred mixture of 2-bromo-5-(methylthio)-1,3,4-thiadiazole (0.22 g, 1.0 mmol) (prepared as described in WO 97/30981), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]isothiazole (0.18 g 0.69 mmol), Na2CO3 (0.22 g, 2.1 mmol), and Pd(PPh3)4 (80 mg, 0.07 mmol) was added EtOH (1.0 mL), water (1.0 mL) and DME (3.0 mL). The resulting mixture was heated at 90° C. overnight and at 140° C. for 30 minutes. The mixture was cooled and passed through a short path of Celite, washing with DCM (3×10 mL). The combined organic phases were concentrated to give the crude residue. Purification by chromatography on silica gel (DCM—5% MeOH in DCM) gave the product as an off-white powder (0.16 g, 87%). LCMS (API-ES) m/z (%): 266.4 (100%, M+H+); 1H NMR (400 MHz, CDCl3): δ ppm 8.97 (s, 1 H) 8.48 (s, 1 H) 8.16 (d, J=8.53 Hz, 1 H) 8.00 (d, J=8.03 Hz, 1 H) 2.87 (s, 3 H).

Provenance & Evidence