Ammonium Chloride → HCID 69434808, compound

Participants

Reaction Conditions

Reaction Steps

4-Bromobenzyloxy-tert-butyldimethylsilane (1.23 g, 4.08 mmol) obtained in Step 1 was dissolved in THF (30 mL) and the flask was filled with argon. The reaction mixture was cooled to −78° C., and a 1.57 mol/L n-butyl lithium-hexane solution (2.60 mL, 4.09 mmol) was added thereto, followed by stirring at same temperature for 5 minutes. A solution of 3-(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)benzaldehyde (0.800 g, 2.72 mmol) obtained in Step 2 in THF (5 mL) was dropped into the mixture for 15 minutes, followed by stirring at −78° C. for 1 hour. The reaction mixture was added with a saturated aqueous ammonium chloride solution to terminate the reaction, and diluted with ethyl acetate. The organic layer was separated from the aqueous layer, and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:2) to obtain [4-(tert-butyldimethylsilyloxymethyl)phenyl][3-(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)phenyl]methanol (0.923 g, yield 66%).

Provenance & Evidence