1-Bromopentane → Ethyl 6-{(E)-2-[3-(difluoromethoxy)-2-(pentyloxy)phenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylate

Participants

Reaction Steps

Alkylation of Intermediate 6 (400 mg, 1.052 mmol) with 1-bromopentane (157 mg, 1.262 mmol) in presence of potassium carbonate (160 mg, 1.157 mmol) in anhydrous N,N-dimethylformamide (4 mL) as described in Intermediate 7A gave 475 mg of the compound as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 0.90 (t, J=7.2 Hz, 3H), 1.30-1.40 (m, 5H), 1.44-1.52 (m, 2H), 1.72-1.78 (m, 2H), 3.93 (t, J=6.6 Hz, 2H), 4.40 (q, J=6.9 Hz, 2H), 7.19 (t, J=73.8 Hz, 1H), 7.21-7.30 (m, 2H), 7.43-7.49 (m, 1H), 7.53-7.58 (m, 1H), 7.77 (d, J=16.2 Hz, 1H), 7.86 (d, J=16.2 Hz, 1H), 8.14 (d, J=4.2 Hz, 1H); ESI-MS (m/z) 451.19 (M+H)+.

Provenance & Evidence