Water → 3-Oxa-8-azabicyclo[3.2.1]octan-8-yl(5-bromo-4-(4-chlorophenyl)thiazol-2-yl)methanone

Temperature

52.5 °C

To a stirred solution 3-oxa-8-azabicyclo[3.2.1]octan-8-yl(4-(4-chlorophenyl)thiazol-2-yl)methanone (Step-2 of compound 68, 0.2 g, 0.60 mmol) in DMF (10 ml) at 0° C. was added N-bromosuccinimide (0.10 g, 0.60 mmol) in a portionwise manner. The resulting reaction mixture was stirred at 50-55° C. for 4 hrs. The progress of reaction was monitored by TLC. The reaction mixture was cooled to room temperature, water (40 ml) was added slowly and aqueous layer was extracted with ethyl acetate (2×50 ml). The organic layer was washed with water (1×30 ml). Combined organic layer was dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to obtain a crude product; which was purified by flash column chromatography using 20% ethyl acetate in hexanes as an eluent to obtain the title compound (0.12 g, 48.6%). MS: m/z 414 (M+1).

1. customThe resulting reaction mixture
2. customThe progress of reaction
3. temperatureThe reaction mixture was cooled to room temperature
4. extractionaqueous layer was extracted with ethyl acetate (2×50 ml)
5. washThe organic layer was washed with water (1×30 ml)
6. dry with materialCombined organic layer was dried over anhydrous Na2SO4
7. customThe solvent was evaporated under reduced pressure
8. customto obtain a crude product
9. customwhich was purified by flash column chromatography

ORD record

ord-f4c6b3019ae747a28ce2e0ee86d17924

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09388196B2