N-Iodosuccinimide → 2-(3,4-Dimethoxy-phenyl)-5-iodo-6-methyl-imidazo[2,1-b][1,3,4]thiadiazole

Participants

Reaction Steps

2-(3,4-dimethoxyphenyl)-6-methylimidazo[2,1-b][1,3,4]thiadiazole (0.346 g, 1.257 mmol) was dissolved in DCM (4.2 mL), and NIS (0.283 mg, 1.257 mmol) was added. The reaction mixture was stirred at RT overnight, quenched with sat. aq. thiosulfate and extracted with DCM. The organic layers were combined and washed with sat. aq. NH4Cl, dried (MgSO4), filtered and concentrated. The residue was suspended in Et2O, and the solid was filtered off, washed with Et2O and dried in vacuo affording the desired product (brown solid (0.295 g, 58%). TLC (cyclohexane/EtOAc 1:1) Rf 0.46; HPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.): tR=4.53 min, [M+H]+ m/z 402.0; 1H NMR (300 MHz, CDCl3) δ/ppm 7.37 (s, 1H), 7.32 (d, J=8.3, 1H), 6.86 (d, J=8.3, 1H), 3.91 (d, J=14.3, 6H), 2.31 (s, 3H).

Provenance & Evidence