Pyridine → HCID 131736060, compound

Participants

Reaction Steps

To a stirred solution of ((2R,3 S,5R)-5-((5-([1,1′-biphenyl]-4-yl)-6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)-3-((triethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)methanol (56 mg, 0.080 mmol) in anhydrous DCM under nitrogen was added pyridine (13 μL, 12.7 mg, 0.161 mmol) and Dess-Martin periodinane (51 mg, 0.121 mmol). After stirring at room temperature for 2 hours, the mixture was directly loaded onto a Biotage™ 10 g silica gel cartridge and eluted with 0-20% EtOAc in 1:1 Hexane/DCM over 20 column volumes. The desired SEM regioisomeric product fractions were combined and concentrated under reduced pressure to provide the title compound as a clear oil. LC-MS: calculated for C36H48ClN3O5Si2 693.28, observed m/e: 694.25 (M+H)+ (Rt 3.23/4 min, minor isomer), 694.23 (M+H)+ (Rt 3.31/4 min, major isomer).

Provenance & Evidence