HCID 13567773, compound → Mdl 20610

Participants

Reaction Conditions

Reaction Steps

A solution of 0.39 g of 3-[2-chloro-5-(methylsulfonyl)-3-pyridinyl]-1-(3,4-dichlorophenyl)propan-1-one in 15 ml of methylene chloride was cooled to -70° C. under nitrogen and then a solution of 1.0 ml of 1.5M diisobutylaluminum hydride/toluene was added dropwise over 3 minutes while keeping the temperature below -65° C. After an additional 5 minutes, the mixture was quenched by careful addition of 1.5 ml of a mixture consisting of 10% water, 40% acetic acid and 50% ether. The reaction mixture was then allowed to warm to 0° C. and was partitioned between water and methylene chloride. The methylene chloride layer was washed with aqueous saturated sodium bicarbonate solution, dried over magnesium sulfate and filtered, and the filtrate was concentrated to a colorless solid, 3-[2-chloro-5-(methylsulfonyl)-3-pyridinyl]-1-(3,4-dichlorophenyl)propan-1-ol. This solid was dissolved in 2 ml of anhydrous dimethyl sulfoxide and added to a stirred suspension of 0.07 g of 50% sodium hydride (previously freed of oil by washing with hexane) in 10 ml of dimethyl sulfoxide under nitrogen. Gas evolution took place and the mixture first became lavender and then cherry red. After 15 minutes, it was partitioned between ethyl acetate and 1N hydrochloric acid. The yellow ethyl acetate layer was washed with water and then twice with aqueous saturated sodium chloride solution, dried over magnesium sulfate and filtered and the filtrate was concentrated to leave a pale yellow solid. This solid was recrystallized from a mixture of 2-propanol and ethyl acetate to give 2-(3,4-dichlorophenyl)-3,4-dihydro-6-(methylsulfonyl)-2H-pyrano[2,3-b]pyridine melting at about 171.5°-172.5° C. This material exhibited the same spectral characteristics as the material prepared by the procedure described in Example 17. This compound has the following structural formula: ##STR7##

Provenance & Evidence