Azobisisobutyronitrile → Ethyl 6-(bromomethyl)imidazo[2,1-b]thiazole-5-carboxylate

To a stirred solution of Step 1 intermediate (2.60 g, 12.366 mmol) and azobisisobutyronitrile (AIBN) (0.041 g, 0.247 mmol) in carbon tetrachloride (40 mL) at reflux temperature was added N-bromosuccinimide (2.40 g, 13.602 mmol). After refluxing for 18 h, the reaction mixture was cooled to room temperature and diluted with ethyl acetate (200 mL) and water (100 mL). The layers were separated. Aqueous layer was extracted with ethyl acetate (2×50 mL) and the combined organic layers were washed with brine (2×50 mL), dried (Na2SO4) and filtered. The filtrate was concentrated under reduced pressure. The residue obtained after the evaporation of the solvent was purified by silica gel column chromatography using 5% ethyl acetate in petroleum ether to obtain 1.95 g of the product as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.36 (t, J=6.6 Hz, 3H), 4.36 (q, J=7.2 Hz, 2H), 4.85 (s, 2H), 7.52 (d, J=4.5 Hz, 1H), 8.10 (d, J=4.5 Hz, 1H); ESI-MS (m/z) 291.58 (MH)+.

1. temperatureAfter refluxing for 18 h
2. customThe layers were separated
3. extractionAqueous layer was extracted with ethyl acetate (2×50 mL)
4. washthe combined organic layers were washed with brine (2×50 mL)
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationThe filtrate was concentrated under reduced pressure
8. customThe residue obtained
9. customafter the evaporation of the solvent
10. customwas purified by silica gel column chromatography

ORD record

ord-c198d030f4da4e1796ef9d74b6695dd1

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318928B2