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

HRID 245950

Reaction equation

HRID 245950 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.[CH3:11][C:12]([Si:15](Cl)([CH3:17])[CH3:16])([CH3:14])[CH3:13].N1C=CN=C1>CN(C=O)C>[C:12]([Si:15]([CH3:17])([CH3:16])[O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2)([CH3:14])([CH3:13])[CH3:11]

Participants

5

Reactant 3

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

Product 1

HCID 580425115-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1H-indazoleYield 93.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a round-bottomed flask, 5-hydroxy-1H-indazole (700 mg, 5.22 mmol) was dissolved in DMF (15 ml) and TBDMS-Cl (865 mg, 5.74 mmol) and imidazole (426 mg, 6.26 mmol) were added. The reaction mixture was stirred at room temperature overnight then quenched with water and extracted with diethyl ether (2×). The combined organic layers were washed twice with water and once with brine then dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-30% EtOAc) to afford 1.21 g (93%) of 5-(tert-butyl-dimethyl-silanyloxy)-1H-indazole as an off-white solid.

Workup

  1. customthen quenched with water
  2. extractionextracted with diethyl ether (2×)
  3. washThe combined organic layers were washed twice with water and once with brine
  4. dry with materialthen dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-30% EtOAc)

Sources & evidence

ORD record
ord-9f54cd4bb5d744ff8e1f5e4078908aa2
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Linked notes

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