N-bromobutanimide → ethyl 2-bromo-5,6-dihydro-4H-thieno[2,3-c]azepine-7(8H)-carboxylate

To a solution of Compound 1044 (1.78 g, 7.90 mmol) in acetonitrile (80 mL) at 0° C. was slowly added NBS (1.69 g, 9.48 mmol). The reaction was stirred at room temperature for 30 minutes, at which point HPLC analysis indicated disappearance of starting material. The reaction was quenched by addition of saturated sodium bicarbonate (50 mL) and stirred for one hour. The reaction was then extracted with diethyl ether (3×100 mL), the organics concentrated, and the residue purified by silica chromatography (5-30% ethyl acetate in hexanes) to give ethyl 2-bromo-5,6-dihydro-4H-thieno[2,3-c]azepine-7(8H)-carboxylate as a pale yellow oil (Compound 1045, 2.07 g, 86% yield); 1H NMR (300 MHz, CDCl3): δ 6.67 (s, 1H), 4.38 (s, 2H), 4.15-3.99 (m, 4H), 3.64 (d, J=3.8 Hz, 2H), 2.73-2.67 (m, 2H) and 1.22-1.09 (m, 3H).

1. customat 0° C.
2. customThe reaction was quenched by addition of saturated sodium bicarbonate (50 mL)
3. stirringstirred for one hour
4. extractionThe reaction was then extracted with diethyl ether (3×100 mL)
5. customthe organics concentrated, and the residue purified by silica chromatography (5-30% ethyl acetate in hexanes)

ORD record

ord-0c71b4302400472bad97a4ed0357d5df

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08481524B2