Cesium carbonate → HCID 67077862, compound

Participants

Reaction Steps

Cs2CO3 (0.22 g, 0.68 mmol) was added to a solution of 3,5-dichloro-pyridine-4-carbaldehyde (0.10 g, 0.57 mmol) and thiazole-2-thiol (0.10 g, 0.85 mmol) in THF (10 mL). After stirring at room temperature overnight, the solvent was removed in vacuo and saturated aqueous NaCl solution (20 mL) and EA (40 mL) were added to the reaction mixture. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo and the residue was used in the following step without further purification. The aldehyde group in 3-chloro-5-(thiazol-2-ylsulfanyl)-pyridine-4-carbaldehyde was reduced as described for the synthesis of (3,5-dichloro-pyridin-4-yl)-methanol to give [3-chloro-5-(thiazol-2-ylsulfanyl)-pyridin-4-yl]-methanol which was used in the following step without further purification. Conversion of [3-chloro-5-(thiazol-2-ylsulfanyl)-pyridin-4-yl]-methanol into 3-chloro-4-chloromethyl-5-(thiazol-2-ylsulfanyl)-pyridine according to the synthesis of 3,5-dichloro-4-chloromethyl-pyridine and subsequent reaction with 2-methyl-4-(1-methyl-1H-imidazol-2-yl)-quinolin-8-ol according to the synthesis of 8-(3,5-dichloro-pyridin-4-ylmethoxy)-4-imidazol-1-yl-2-methylquinoline yielded the title compound as the TFA salt. MS (m/z): 480.2 [M+H+].

Provenance & Evidence