Toluene → 7-Cyclopropyl-1,3-benzothiazole

Temperature

100 °C

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.

1. customAfter degassed under vacuum
2. customflushed with nitrogen
3. temperaturecooled down to room temperature
4. customquenched by the addition of 20.0 mL of water
5. extractionextracted with ethyl acetate (3×20 mL)
6. washThe combined organic layers were washed with brine
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationUpon filtration and concentration under reduced pressure
9. customthe residue was purified by flash chromatography on silica gel
10. washeluting with petroleum ether/ethyl acetate (10:1-5:1)

ORD record

ord-33eafef5b0384c36b01645edecddc1a8

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221809B2