Water → 2-Bromo-5-(4-isopropoxyphenoxy)-1,3,4-thiadiazole

Temperature

85 °C

A solution of Example 24B (1.4 g, 5.11 mmol) in N,N-dimethyl formamide (20 mL) was treated with K2CO3 (1.06 g, 7.66 mmol) and 2-iodopropane (5.1 mL, 51.1 mmol) and the reaction mixture was sealed in a screw-top pressure vessel and heated at 85° C. for 2 hours. The reaction was cooled to 25° C., poured into water (200 mL), and extracted with diethyl ether (2×100 mL). The combined organic layers were washed with water (3×80 mL) and brine (80 mL), dried (Na2SO4), filtered and evaporated to provide 1.6 g of a light brown solid. The residue was purified by flash chromatography on silica gel eluting with a solvent gradient from 1% to 14% ethyl acetate in hexanes to provide 0.8 g (50%) of the title compound as a clear colorless oil. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.37 (d, J=9.19 Hz, 2H) 7.01 (d, J=9.19 Hz, 2H) 4.63 (heptet, J=5.88 Hz, 1H) 1.27 (d, J=5.88 Hz, 6H); MS (ESI) m/z 316.9 (M+H)+.

1. customthe reaction mixture was sealed in a screw-top pressure vessel
2. temperatureThe reaction was cooled to 25° C.
3. extractionextracted with diethyl ether (2×100 mL)
4. washThe combined organic layers were washed with water (3×80 mL) and brine (80 mL)
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. customevaporated

ORD record

ord-60548d79cb5c4d238a3dab5b9a7a9ab2

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08748627B2