Trityl chloride → 6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridine

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Reaction Steps

Under ice-cooling, a solution of 6-chloro-1H-pyrazolo[4,3-c]pyridine (1 g, 6.51 mmol) in THF (40 mL), was treated with NaH (60% in mineral oil; 438 mg, 10.95 mmol) and the mixture was stirred for 1 h. Trityl chloride (2.17 g, 7.81 mmol) was added and the mixture was stirred at the same temperature for 1 h and further stirred at room temperature for 3 h. The mixture was quenched with saturated NH4Cl and then extracted with EtOAc. The organic layer was washed with water, brine, dried (MgSO4) and concentrated in vacuo. To the residue was added 10 ml of DCM, some solid precipitated out. After filtration, some yellow solid was afforded. The filtrate was purified by chromatography on silica gel (0-30% EtOAc in hexane) to isolate 6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridine (1.375 g, 3.47 mmol, 53% overall) as a yellow solid. MS ESI calc'd. for C25H19ClN3 [M+H]+ 396, found 396.

Provenance & Evidence