Tetrabutylammonium Fluoride → HCID 67777804, compound

HRID 1026303Notes

Reaction equation

HRID 1026303 reaction equation
[Cl:1][C:2]1[C:10]2[C:6](=[CH:7][N:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][Si](C(C)C)(C(C)C)C(C)C)=[CH:13][CH:12]=3)[N:9]=2)[CH:5]=[CH:4][C:3]=1[O:28][CH2:29][CH:30]1[CH2:32][CH2:31]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:1][C:2]1[C:10]2[C:6](=[CH:7][N:8]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[N:9]=2)[CH:5]=[CH:4][C:3]=1[O:28][CH2:29][CH:30]1[CH2:31][CH2:32]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67778381HCID 67778381, compound

Product 1

HCID 67777804HCID 67777804, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 7-chloro-6-(cyclopropylmethoxy)-2-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)-2H-indazole (112 mg) in THF (1 mL) was added a THF solution (1.0 M, 0.71 mL) of tetrabutylammonium fluoride at room temperature, and the mixture was stirred for 1 hr. The solvent was evaporated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The separated aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as colorless crystals (44.6 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. extractionThe separated aqueous layer was extracted again with ethyl acetate
  5. washThe combined organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-51ec650f88684035a6a801848403e4ad
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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