1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-(4-methanesulfonyl-piperidin-1-yl)-1-(2-methylsulfanyl-pyrimidin-4-yl)-1H-indazole

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Reaction Conditions

Reaction Steps

In a 50 ml, round bottom flask, 2-fluoro-6-(4-methanesulfonylpiperidine-1-yl)benzaldehyde (1.37 g, 4.8 mmol), N-(2-methylsulfanyl-pyrimidin-4-yl)-hydrazine (0.75 g, 4.8 mmol) and DBU (2.19 g, 14.4 mmol) were combined with DMSO (17 mL). The mixture was stirred at 180° C. for 1.5 hr in a microwave. The brown solution was blown to dryness and the residue was purified through ISCO flash column chromatography (30% to 100% ethyl acetate in hexanes) to provide 4-(4-methanesulfonyl-piperidin-1-yl)-1-(2-methylsulfanyl-pyrimidin-4-yl)-1H-indazole as a pale orange solid (750 mg, 38.7% yield). LC-MS calcd for C18H21N5O2S2 (m/e) 403.11, obsd 404.0 (M+H).

Provenance & Evidence