N-bromobutanimide → HCID 58293758, compound

Participants

Reaction Steps

To a solution of Compound 1050 (1.53 g, 6.79 mmol) in acetonitrile (70 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 mixture was extracted with diethyl ether (3×100 mL), the volatiles removed under reduced pressure, and the residue purified by silica chromatography (0-30% ethyl acetate in hexanes) to give ethyl 2-bromo-7,8-dihydro-4H-thieno[3,2-c]azepine-5-carboxylate as a pale yellow oil (Compound 1051, 2.07 g, 86% yield); 1H NMR (300 MHz, CDCl3): δ 6.84-6.70 (m, 1H), 4.30 (d, J=15.4 Hz, 2H), 4.02 (q, J=6.7 Hz, 2H), 3.63 (s, 2H), 2.78 (dd, J=4.6, 5.7 Hz, 2H), 1.80 (s, 2H) and 1.16 (t, J=6.8 Hz, 3H).

Provenance & Evidence