Diisopropylethylamine → 8-(4-Bromothiazol-2-yl)-3-oxa-8-azabicyclo[3.2.1]octane

Temperature

80 °C

To a stirred solution of 2,4-dibromothiazole (0.585 g, 2.41 mmol) in DMF (10 ml) were added 3-oxa-8-azabicyclo[3.2.1]octane (prepared according to the procedure given in WO 2010/120854, 0.3 g, 2.65 mmol) and DIPEA (0.47 gm, 0.63 ml, 3.62 mmol) under a stream of nitrogen. The reaction mixture was then stirred at 80° C. for 18 hrs and the progress of reaction was monitored by TLC. The reaction mixture was cooled to room temperature; quenched with cold water (20 ml) and extracted with ethyl acetate (3×30 ml). The combined organic layer was washed with water (2×10 ml), dried over sodium sulphate and concentrated to give crude compound; which was purified by flash column chromatography using 20% ethyl acetate in hexanes as an eluent to obtain the title compound (0.31 g, 46.7%). MS: m/z 276 (M+1).

1. customprepared
2. customthe progress of reaction
3. temperatureThe reaction mixture was cooled to room temperature
4. customquenched with cold water (20 ml)
5. extractionextracted with ethyl acetate (3×30 ml)
6. washThe combined organic layer was washed with water (2×10 ml)
7. dry with materialdried over sodium sulphate
8. concentrationconcentrated
9. customto give crude compound
10. customwhich was purified by flash column chromatography

ORD record

ord-4f6caad018ac4b169c6bc72ee30422cf

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09388196B2