Sodium Thiosulfate → HCID 86724132, compound

HRID 1748803Notes

Reaction equation

HRID 1748803 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Br:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]([C:34]2[C:35]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][N:50]=3)=[N:36][N:37]([CH2:47][CH3:48])[C:38]=2[NH:39][C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[CH2:31][CH2:32][OH:33])=[CH:26][CH:25]=1.C([O-])(O)=O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.O>[Br:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]([C:34]2[C:35]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][N:50]=3)=[N:36][N:37]([CH2:47][CH3:48])[C:38]=2[NH:39][C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:43])[CH3:44])[CH2:31][CH:32]=[O:33])=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087Triacetoxyperiodinane2×HCID 516892Sodium BicarbonateHCID 86724130HCID 86724130, compound

Product 1

HCID 86724132HCID 86724132, compoundYield 35.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

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)+.

Workup

  1. customthe ice bath was removed
  2. waitAfter about 30 min
  3. waitAfter about 30 min
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted with DCM (10 mL)
  6. dry with materialThe combined organics were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified on silica gel using a gradient of 20-75% EtOAc in heptane
  10. additionThe fractions containing product
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-029dd0288b2f4f818b737a817d39987e
Source dataset
uspto-grants-2015_10
Patent number
US09150592B2

Reaction notes

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