Toluene → HCID 25261339, compound

Participants

Reaction Steps

5-Benzyloxy-2-bromo-pyridine (0.25 mmol), sodium-tert.-butylate (1.4 eq.), tris-(dibenzylideneaceton)-dipalladium (0.1 eq.), bis(2-diphenylphosphinophenyl)-ether (0.4 eq.) and 2-amino-thiazole (1.5 eq.) are filled under nitrogen in a microwave reaction vessel. Degassed toluene (45 eq.) is added. The reaction suspension is heated for 60 min to 150° C. and 60 minutes to 180° C. Ethyl acetate is added to the reaction suspension and filtrated over celite. The solvent of the filtrate is removed in vacuo. (5-Benzyloxy-pyridine-2-yl)-thiazole-2-yl-amine (“A30”) is obtained after reversed phase column chromatography (water/acetonitrile+0.1% TFA) as orange oil in a yield of 34%. HPLC (method C): 1.69 min; LC-MS (method A): 1.44 min, 285.15 (MH+); 1H-NMR (DMSO-d6, 500 MHz): δ [ppm] 11.108 (s, 1H), 8.072 (d, 1H, J=2.9 Hz), 7.500-7.447 (m, 3H), 7.412-7.383 (m, 2H), 7.349-7.320 (m, 2H), 7.064 (d, 1H, J=9 Hz), 6.926 (d, 1H, J=3.5 Hz), 5.139 (s, 2H).

Provenance & Evidence