Sodium periodate → HCID 178466767, compound

HRID 2220137Notes

Reaction equation

HRID 2220137 reaction equation
[C:1]([O:5][C:6]([N:8]([C:18]1[N:23]2[N:24]=[CH:25][CH:26]=[C:22]2[C:21]([C:27]#[N:28])=[C:20]([OH:29])[C:19]=1[CH2:30][CH:31]=C)[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=[O:34].[Na+]>O1CCCC1.O.C(OCC)(=O)C.S([O-])([O-])(=O)=S.[Na+].[Na+].[Os](=O)(=O)(=O)=O>[C:1]([O:5][C:6]([N:8]([C:18]1[N:23]2[N:24]=[CH:25][CH:26]=[C:22]2[C:21]([C:27]#[N:28])=[C:20]([OH:29])[C:19]=1[CH2:30][CH2:31][OH:34])[C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH3:17])=[CH:13][CH:14]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

8

Reactant 2

HCID 23667635Sodium periodateHCID 178439716HCID 178439716, compound

Product 1

HCID 178466767HCID 178466767, compoundYield 51.1%

Reagents, catalysts & solvents 5

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 24477Sodium ThiosulfateSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butoxy-N-[4-cyano-5-hydroxy-6-(2-propenyl)pyrazolo[1,5-a]pyridin-7-yl]-N-(4-ethoxyphenyl)carboxamide (27) (248 mg) was dissolved in a mixture of tetrahydrofuran (4.6 mL) and water (1.1 mL). To this solution, sodium periodate (611 mg) was added and the solution was cooled to 0° C. To this solution, osmium tetroxide (0.58 mL, 2.5 wt. % 2-methyl-2-propanol solution) was added dropwise and the mixture was stirred at room temperature for 2 h. The reaction solution was diluted with ethyl acetate and aqueous sodium thiosulfate solution was added to quench the reaction. After the organic layer was separated, the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with a mixture of brine and saturated aqueous ammonium chloride solution (9:1) and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was dissolved in methanol (5.7 mL). Here sodium borohydride (21.6 mg) was added and the solution was stirred at room temperature for 1 h. The reaction solution was diluted with ethyl acetate and washed with brine. The organic layer was dried over sodium sulfate, the solvent was removed under reduced pressure and the resultant crude product was purified with silica-gel column chromatography (hexane/ethyl acetate=2/1 to 1/2) to obtain the title compound (42) (128 mg, Yield 51%).

Workup

  1. additionwas added
  2. customto quench
  3. customthe reaction
  4. customAfter the organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic layers were washed with a mixture of brine and saturated aqueous ammonium chloride solution (9:1)
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was removed under reduced pressure
  9. dissolutionthe residue was dissolved in methanol (5.7 mL)
  10. additionHere sodium borohydride (21.6 mg) was added
  11. stirringthe solution was stirred at room temperature for 1 h
  12. additionThe reaction solution was diluted with ethyl acetate
  13. washwashed with brine
  14. dry with materialThe organic layer was dried over sodium sulfate
  15. customthe solvent was removed under reduced pressure
  16. customthe resultant crude product was purified with silica-gel column chromatography (hexane/ethyl acetate=2/1 to 1/2)

Sources & evidence

ORD record
ord-d852184477c34b70bbe27c1ee680194a
Source dataset
uspto-grants-2008_08
Patent number
US07417053B2

Reaction notes

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