Dichloromethane → 6-(2,6-dichloro-3,5-dimethoxyphenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine

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Reaction Steps

At r.t. to a solution of 6-(3,5-dimethoxyphenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine (0.66 g, 1.9 mmol) in methylene chloride (10 mL) with stirring was added drop-wise sulfuryl chloride (300 μL, 3.7 mmol)(Acros Organics, Cat. No. 37815). The mixture was stirred at r.t. for 2 h. LCMS showed 25% product formed, and 75% was mono-chlorinated product. Additional sulfuryl chloride (100 μL) was added to the mixture. It was stirred at r.t. for 5 h, and then concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (0.78 g). LCMS (M+H)+=408.0.

Provenance & Evidence