Carbon Tetrachloride → HCID 18446626, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-cyclopentyl-4-[2-(2-methyl-1,3-thiazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyridinamine (138 mg, 0.37 mmol) in tetrahydrofuran (10 mL) was cooled to −78° C. n-Butyl lithium (1.6M in hexanes, 0.75 mL, 1.22 mmol) was added dropwise. After stirring at −78° C. for 20 minutes, carbon tetrachloride (1 mL) was added to the solution. The reaction was stirred for another 20 minutes at −78° C. and subsequently quenched with water. The reaction mixture was warmed to room temperature and extracted with ethyl acetate. The organics were combined and washed with water, brine and dried over magnesium sulfate. Filtration and concentration, followed by flash chromatography (1:19 methanol/dichloromethane) gave 4-[7-chloro-2-(2-methyl-1,3-thiazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyridinamine as a brown oil.

Provenance & Evidence