Sodium Thiosulfate → HCID 86724132, compound

Participants

Reaction Conditions

Reaction Steps

Dess-Martin periodinane (0.203 g, 0.480 mmol) was added in one portion to a solution of tert-butyl (4-(1-(4-bromophenyl)-3-hydroxypropyl)-1-ethyl-3-(pyridin-2-yl)-1H-pyrazol-5-yl)carbamate (0.334 g, 0.480 mmol) and DCM (5.00 mL) under N2 at about 0° C. After about 5 min, the ice bath was removed. After about 30 min, Dess-Martin periodinane (0.203 g, 0.480 mmol) was added in one portion. After about 30 min, the reaction mixture was cooled to 0° C. then saturated aqueous NaHCO3 (5 mL), water (5 mL), 10% aqueous sodium thiosulfate (5 mL), and DCM (10 mL) were added. After stirring vigorously for about 15 min, the layers were separated and the aqueous layer was extracted with DCM (10 mL). The combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified on silica gel using a gradient of 20-75% EtOAc in heptane. The fractions containing product were combined and concentrated under reduced pressure to afford tert-butyl (4-(1-(4-bromophenyl)-3-oxopropyl)-1-ethyl-3-(pyridin-2-yl)-1H-pyrazol-5-yl)carbamate (0.0848 g, 0.170 mmol, 35%) as a pale yellow solid. LC-MS (Table 1, Method g) Rt=2.61 min; m/z 499 and 501 (M+H)+.

Provenance & Evidence