4-Methylbenzaldehyde → [3-(2-Chloro-phenyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]-p-tolyl-methanol

Participants

Reaction Conditions

Reaction Steps

In a flame-dried flash under nitrogen a solution of 6-bromo-3-(2-chloro-phenyl)-[1,2,4]triazolo[4,3-a]pyridine (205 mg, 0.66 mmol) in THF (2.5 mL) was cooled to 0° C. A solution of isopropylmagnesium chloride (1.3 eq) was added dropwise, followed by 4-methylbenzaldehyde (1 equivalent), and the resulting mixture was warmed to 50° C. for 3 hours. The reaction was cooled and quenched with water/ethyl acetate. The organic layer was separated, concentrated in vacuo, and the residue purified by flash chromatography (eluting with 80% ethyl acetate/hexane) to give the title compound (67 mg, 29%). MS (M+1)=350.5.

Provenance & Evidence