Sodium Iodide → ethyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-iodopropyl)thiazole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To ethyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-chloropropyl)thiazole-4-carboxylate (2B) (9.3 g, 17.2 mmol) in acetonitrile (125 mL) was added sodium iodide (25.8 g, 172 mmol). The reaction mixture was purged with nitrogen twice. The reaction mixture was then heated at 90° C. for 5 hours, cooled to rt, and concentrated under reduced pressure. The concentrate was diluted with EtOAc, washed with water, brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was slurried in Et2O, filtered, washed with additional Et2O and dried under reduced pressure to provide the desired product ethyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-iodopropyl)thiazole-4-carboxylate (2C) in 93% yield. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.89 (1H, s), 8.04 (1H, d), 7.79 (1H, d), 7.66 (1H, d), 7.43 (4H, m), 4.83 (2H, s), 4.19 (2H, q), 3.72 (2H, t), 3.26 (2H, t), 3.06 (4H, m), 2.03 (2H, m), 1.21 (3H, t).

Provenance & Evidence