Triethylamine → HCID 66883417, compound

Participants

Reaction Steps

To a solution of 2-[2-(4-bromofuran-2-yl)-2-oxoethyl]-6-chloro-N-(2,4-difluorobenzyl)benzamide (2.4 g, 5.1 mmol), prepared in a manner similar to that described above in Paragraph B, in dioxane (30 mL) was added 4-toluenesulfonic acid monohydrate (450 mg, 2.4 mmol). The resulting solution was heated to reflux. After 20 hours at reflux the reaction solution was allowed to cool to ambient temperature, and treated with Et3N (2.0 mL, 14 mmol). The crude product was purified by adsorbing the material onto silica gel from the reaction solution, loading the resulting solid onto the column and eluting with a gradient from 10% to 50% EtOAc in hexane containing 10% CH2Cl2 (to improve the solubility of the product). The broad peak that eluted was collected to afford 3-(4-bromofuran-2-yl)-8-chloro-2-(2,4-difluorobenzyl)-2H-isoquinolin-1-one (1.9 g, 82% yield) as a brown powder. 1H-NMR (400 MHz, CDCl3): δ 7.56-7.51 (2H, m), 7.47 (1H, d, J=0.8 Hz), 7.43 (1H, dd, J=6.3, 2.8 Hz), 7.06-6.99 (1H, m), 6.79-6.73 (2H, m), 6.68 (1H, s), 6.49 (1H, d, J=0.8 Hz), 5.32 (2H, s).

Provenance & Evidence