6-Bromo-2-phenylimidazo[1,2-a]pyridine → [4-(2-Phenylimidazo[1,2-a]pyridin-6-yl)phenyl]methanol

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Reaction Steps

150 mg of 6-bromo-2-phenylimidazo[1,2-a]pyridine, 125 mg of 4-(hydroxymethyl)phenylboronic acid, 19 mg of tetrakis(triphenylphosphine)palladium and 2 ml of acetonitrile are placed in a microwave tube. Under a stream of nitrogen, 2 ml of nitrogen-degassed toluene and then 2 ml of a 2M solution of sodium carbonate are added thereto. The tube is placed in a microwave device and irradiated at 150° C. for 15 min. The organic phase is recovered, dried and then concentrated under reduced pressure. The residue is taken up with diisopropyl ether and the precipitate is recovered by filtration, washed and dried. It is purified by recrystallization from n-butanol. 52 mg of compound are obtained. Mp=238-240° C. 1H NMR (DMSO-d6, δ in ppm): 4.54 (d, J=5.5 Hz, 2H); 5.2 (t, J=5.6 Hz, 1H); from 7.24 to 7.73 (m, 9H); 7.96 (m, 2H); 8.36 (s, 1H); 8.84 (t, J=1.3 Hz, 1H). M+H=301.

Provenance & Evidence