Tetrahydrofuran → HCID 58042438, compound

HRID 2048064Notes

Reaction equation

HRID 2048064 reaction equation
[H-].[Na+].[Si:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][N:15]=[CH:14]2)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[CH2:20]1[CH2:24]OC[CH2:21]1>CCOC(C)=O>[Si:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH:20]([CH3:24])[CH3:21])[N:15]=[CH:14]2)([C:6]([CH3:9])([CH3:7])[CH3:8])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 580425115-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1H-indazole

Product 1

HCID 58042438HCID 58042438, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% oil dispersion, 211 mg, 5.28 mmol) was added to a solution of 5-{[tert-butyl(dimethyl)silyl]oxy}-1H-indazole (Preparation 41, 1.09 g, 4.40 mmol) in THF (10 mL) and stirred at room temperature for 15 minutes. The solution was then heated at 50° C. for 18 hours, then at reflux for 8 hours. The reaction mixture was diluted with EtOAc and washed with water, 0.5 N aqueous citric acid solution and brine, then dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting residue was purified by silica gel chromatography eluting with 0 to 10% EtOAc in heptane to yield the title compound as a clear oil (261 mg, 20%):

Workup

  1. temperatureThe solution was then heated at 50° C. for 18 hours
  2. temperatureat reflux for 8 hours
  3. washwashed with water, 0.5 N aqueous citric acid solution and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by silica gel chromatography
  8. washeluting with 0 to 10% EtOAc in heptane

Sources & evidence

ORD record
ord-8c15935d2fe5449dbec3cf7131823661
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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