1-Bromo-3-methylbutane → Ethyl 6-{(E)-2-[3-(difluoromethoxy)-2-(3-methylbutoxy)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-bromo-3-methylbutane (159 mg, 1.262 mmol) in presence of potassium carbonate (159 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 0.93 (t, J=6.6 Hz, 6H), 1.40 (t, J=7.2 Hz, 3H), 1.66 (q, J=6.3 Hz, 2H), 1.82-1.90 (m, 1H), 3.96 (t, J=6.3 Hz, 2H), 4.40 (q, J=6.9 Hz, 2H), 7.19 (t, J=71.4 Hz, 1H), 7.20-7.28 (m, 2H), 7.42-7.50 (m, 1H), 7.53-7.60 (m, 1H), 7.80 (s, 2H), 8.13 (d, J=4.2 Hz, 1H); APCI-MS (m/z) 451.23 (M+H)+.

Provenance & Evidence