2-Pyrrolidone → HCID 89813516, compound

A solution of methyl 4-bromo-2-(bromomethyl)thiazole (prepared according to the procedure reported in US 2010/298388), (0.50 g, 1.94 mmol) in THF (5 ml) was added to a solution of sodium hydride (0.12 g 60% in paraffin oil, 2.92 mmol) and pyrrolidin-2-one (0.20 g, 2.33 mmol) in DMF (5 ml) at 0° C. under stirring. The reaction mixture was stirred at room temperature for 30 minutes. The progress of the reaction was monitored by TLC. The reaction mixture was quenched with water (5 ml). The mixture was then extracted with ethyl acetate (2×50 ml). The combined organic layer was dried over anhydrous Na2SO4. The solvent was evaporated from the dried organic layer under reduced pressure to obtain a crude product; the crud product was further purified by flash column chromatography using 60% ethyl acetate in hexanes as an eluent to obtain the title compound (0.40 g, 79%). MS: m/z 262 (M+1).

1. stirringThe reaction mixture was stirred at room temperature for 30 minutes
2. customThe reaction mixture was quenched with water (5 ml)
3. extractionThe mixture was then extracted with ethyl acetate (2×50 ml)
4. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
5. customThe solvent was evaporated from the dried organic layer under reduced pressure
6. customto obtain a crude product
7. customthe crud product was further purified by flash column chromatography

ORD record

ord-91c6e36ff546430e9ab37da1ae9ab8f3

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09388196B2