Imidazole → 4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1H-indazole

HRID 1159001Notes

Reaction equation

HRID 1159001 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([OH:11])=[CH:8][CH:7]=[CH:6][C:5]=2[NH:4][N:3]=1.N1C=CN=C1.[C:17]([Si:21]([CH3:24])([CH3:23])Cl)([CH3:20])([CH3:19])[CH3:18].O>CN(C)C=O>[C:17]([Si:21]([CH3:24])([CH3:23])[O:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[C:2]([CH3:1])=[N:3][NH:4]2)([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 178434282HCID 178434282, compound

Product 1

HCID 1784342904-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1H-indazoleYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-methyl-1H-indazol-4-ol (0.13 g, 0.90 mmol) in N,N-dimethylformamide (10 ml) was added imidazole (0.31 g, 4.52 mmol) and tert-butyldimethylchlorosilane (0.16 g, 1.04 mmol) at 0° C. Following stirring at room temperature for 12 hours and the addition of distilled water (10 ml), the reaction mixture was extracted three times with ethyl acetate, washed with distilled water and brine, dried over magnesium sulfate, filtered, and concentrated using vacuum evaporation. The crude product was purified by chromatography on silica gel to give 0.21 g of 4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1H-indazole (Yield 89%).

Workup

  1. extractionthe reaction mixture was extracted three times with ethyl acetate
  2. washwashed with distilled water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customvacuum evaporation
  7. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-2a43b768ae12429895196f2c2cb06cc2
Source dataset
uspto-grants-2010_10
Patent number
US07812045B2

Reaction notes

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