Toluene → HCID 24856032, compound

Participants

Reaction Steps

Under a stream of nitrogen, 500 mg of 6-bromo-2-(naphthalen-2-yl)imidazo[1,2-a]pyridine, 235 mg of 3-(hydroxymethyl)phenylboronic acid and 90 mg of tetrakis(triphenylphosphine)palladium are placed in a microwave tube containing 5 ml of toluene degassed beforehand under a stream of nitrogen, 5 ml of acetonitrile and 6 ml of a 0.5M solution of sodium carbonate. The tube is placed in a microwave apparatus and irradiated at 150° C. for 15 min. The organic phase is separated and dried and the filtrate is concentrated under reduced pressure. The residue obtained is taken up with 5 ml of dichloromethane. A precipitate forms and is recovered by filtration, washed with dichloromethane and then with diisopropyl ether and dried under reduced pressure. The experiment is repeated several times (6) and the solids are combined. 2.2 g of compound are obtained and are recrystallized from a 1/1 n-propanol/water mixture. The precipitate is filter-dried, washed with diisopropyl ether and dried under reduced pressure. 1.96 g of compound are obtained. Mp=161-163° C. 1H NMR (DMSO-d6, δ in ppm): 4.58 (d, J=5.5 Hz, 2H); 5.24 (t, J=5.7 Hz, 1H); from 7.29 to 7.73 (m, 8H); from 7.86 to 8.13 (m, 4H); 8.52 (m, 2H); 8.84 (m, 1H). M+H=351.

Provenance & Evidence