1-Bromo-3-methylbutane → Ethyl 2-{(E)-2-[3-(Difluoromethoxy)-2-(3-methylbutoxy)phenyl]vinyl}imidazo[1,2-a]pyridine-3-carboxylate

Participants

Reaction Steps

Alkylation of Intermediate 12 (400 mg, 1.069 mmol) with 1-bromo-3-methylbutane (193.8 mg, 1.283 mmol) in presence of potassium carbonate (163 mg, 1.175 mmol) in anhydrous N,N-dimethylformamide (4 mL) as described in Intermediate 7A, Step 1 gave 480 mg of the compound as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 0.94 (d, J=6.9, 6H), 1.40-1.47 (m, 3H), 1.64-1.71 (m, 2H), 1.88-1.95 (m, 1H), 3.97-4.03 (m, 2H), 4.40-4.48 (m, 2H), 7.12-7.20 (m, 2H), 7.21 (t, J=74.7 Hz, 1H), 7.22-7.28 (m, 1H), 7.53-7.62 (m, 2H), 7.74 (d, J=8.4 Hz, 1H), 7.94 (d, J=15.9 Hz, 1H), 8.04 (d, J=16.2 Hz, 1H), 9.23 (d, J=6.3 Hz, 1H); ESI-MS (m/z) 445.25 (M)+.

Provenance & Evidence