Toluene → 7-Cyclopropyl-1,3-benzothiazole

Participants

Reaction Conditions

Reaction Steps

Into a solution of 7-chloro-1,3-benzothiazole (390 mg, 2.30 mmol, 1.00 equiv), cyclopropylboronic acid (300 mg, 3.49 mmol, 2.00 equiv) and potassium phosphate (2.2 g, 4.50 equiv) in a mixture toluene (12 mL) and water (1.2 mL) was added Pd(OAc)2 (51.6 mg, 0.23 mmol, 0.10 equiv) and PCy3HBF4 (0.17 g, 0.20 equiv). After degassed under vacuum and flushed with nitrogen, the resulting mixture was heated for 6 h at 100° C. in an oil bath under nitrogen atmosphere, cooled down to room temperature, quenched by the addition of 20.0 mL of water and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine and dried over anhydrous sodium sulfate. Upon filtration and concentration under reduced pressure, the residue was purified by flash chromatography on silica gel, eluting with petroleum ether/ethyl acetate (10:1-5:1) to provide the title compound as purple oil. MS m/z [M+H]+ (ESI): 176.

Provenance & Evidence