Diisopropylethylamine → 2-(3-Azabicyclo[3.1.0]hexan-3-yl)-4-bromothiazole

Temperature

80 °C

To a stirred solution of 2,4-dibromothiazole (0.5 g. 2.06 mmol) in DMF (15 ml) were added 3-azabicyclo[3.1.0]hexane hydrochloride (prepared according to the procedure given in Bioorganic and Medicinal Chemistry Letters, 2005, 15, 2093-2096, 0.27 g, 2.26 mmol) and DIPEA (0.80 g, 1.0 ml, 6.17 mmol) under a stream of nitrogen. The reaction was then stirred at 80° C. for 18 hrs; the progress of reaction was monitored by TLC. The reaction was 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 10% ethyl acetate in hexanes as an eluent to obtain the title compound (0.29 g, 58.5%). MS: m/z 246 (M+1).

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

ORD record

ord-9b341d04c11741e996a5a67d278c6002

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09388196B2