Tetrabutylammonium Fluoride → [2-(Benzhydrylidene-amino)-3-fluoropyridin-4-yl]-methanol

HRID 599859Notes

Reaction equation

HRID 599859 reaction equation
[C:1](=[N:14][C:15]1[C:20]([F:21])=[C:19]([CH2:22][O:23][Si](C(C)(C)C)(C)C)[CH:18]=[CH:17][N:16]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(OCC)(=O)C>[C:1](=[N:14][C:15]1[C:20]([F:21])=[C:19]([CH2:22][OH:23])[CH:18]=[CH:17][N:16]=1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59139248Benzhydrylidene-[4-(tert-butyldimethylsilyloxymethyl)-3-fluoropyridin-2-yl]-amine

Product 1

HCID 59139234[2-(Benzhydrylidene-amino)-3-fluoropyridin-4-yl]-methanol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of benzhydrylidene-[4-(tert-butyldimethylsilyloxymethyl)-3-fluoropyridin-2-yl]-amine (14 mg, 32 μmol) and tetrabutylammonium fluoride (1 mol/L in THF) (65 μL, 65 μmol) in THE (0.5 mL) was stirred at room temperature for 30 minutes. Ethyl acetate was then added to the reaction solution, and the solution was washed with sodium hydrogen carbonate solution and saturated saline. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. The resultant residue was purified by silica gel column chromatography to yield the title compound.

Workup

  1. washthe solution was washed with sodium hydrogen carbonate solution and saturated saline
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled away under reduced pressure
  4. customThe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0da9b75b44e5436190e2482b6dbdb79d
Source dataset
uspto-grants-2011_03
Patent number
US07897792B2

Reaction notes

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