Citric Acid → 5-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1H-indazole

HRID 2048065Notes

Reaction equation

HRID 2048065 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[Si:11]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1014381H-Indazol-5-ol

Product 1

HCID 580425115-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1H-indazoleYield 91.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Hydroxyindazole (3.00 g, 22.37 mmol), tert-butyldimethylsilyl chloride (4.05 g, 26.8 mmol) and imidazole (2.28 g, 33.5 mmol) were mixed in DCM (50 mL) and stirred at room temperature for 18 hours. The reaction mixture was poured into 0.5 N aqueous citric acid solution and extracted with DCM (3×25 mL). The combined organics were dried over magnesium sulfate, filtered and evaporated to dryness. The residue was purified by silica gel chromatography eluting with 0 to 50% EtOAc in hexane to yield the title compound as an orange solid (5.09 g, 90%):

Workup

  1. extractionextracted with DCM (3×25 mL)
  2. dry with materialThe combined organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 0 to 50% EtOAc in hexane

Sources & evidence

ORD record
ord-4bec9a3dc4e44ddfacb1cfb05a5b9167
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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