2-BroMo-5,6-dihydro-4H-cyclopenta[d]thiazole synthesis

Yield:1080642-17-6 14%

Reaction Conditions:

with copper(I) bromide;isopentyl nitrite in acetonitrile at 20; for 4 h;

Steps:

39.2

A solution of 5,6-dihydro-4H-cyclopenta[d]thiazol-2-amine (4 g, 28.5 mmol) and isoamyl nitrite (4.2 ml, 31.4 mmol) in CH₃CN (100 ml) was treated with CuBr (6.14 g, 42.8 mmol), added portion-wise, and the reaction was stirred at RT for 4 hours. Silica gel (15 g) was added, the volatiles were removed under reduced pressure, and the crude residue was purified by flash column chromatography (hexane/AcOEt, 98:2 to 9:1) to afford the desired product (779 mg, 14% yield). ESIMS (m/z): 206.0 (MH⁺).

References:

US2010/227859,2010,A1 Location in patent:Page/Page column 87