Ethyl Acetate → [2-(Benzhydrylidene-amino)-3-fluoropyridin-4-yl]-methanol

HRID 1046813Notes

Reaction equation

HRID 1046813 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>C1COCC1>[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

5

Reactant 3

HCID 8857Ethyl AcetateHCID 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 8028TetrahydrofuranSolvent

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 THF (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-09a60985dfd949358b985696418b7540
Source dataset
uspto-grants-2013_10
Patent number
US08569378B2

Reaction notes

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