Tetrabutylammonium Fluoride → HCID 86229373, compound

HRID 1948280Notes

Reaction equation

HRID 1948280 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12](=[O:28])[N:13]([CH2:15][C:16]3[CH:17]=[N:18][C:19]([C:22]#[C:23][Si](C)(C)C)=[CH:20][CH:21]=3)[CH:14]=2)=[CH:5][CH:4]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O>[C:22]([C:19]1[N:18]=[CH:17][C:16]([CH2:15][N:13]2[CH:14]=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[CH:10]=[CH:11][C:12]2=[O:28])=[CH:21][CH:20]=1)#[CH:23]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69349409HCID 69349409, compound

Product 1

HCID 86229373HCID 86229373, compoundYield 35.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(4-methoxyphenyl)-1-((6-(2-(trimethylsilyl)ethynyl)pyridin-3-yl)methyl)pyridin-2(1H)-one (0.60 mmol, 240 mg), tetrabutylammonium fluoride (1.20 mmol, 1.2 mL) in THF (5 mL) and H2O (1 mL) was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure. The residue was taken up in CH2Cl2, washed with water, dried (Na2SO4) and evaporated under reduced pressure. The residue was purified in a manifold (vac.) using a Sep-Pak silica cartridge CH2Cl2/MeOH(NH3)sat. 3%. The fractions were collected and evaporated. The residue thus obtained was triturated with diisopropyl ether. The precipitated solid was filtered off and dried. Further purification by circular chromatography-TLC CH2Cl2/MeOH(NH3)sat. 3% yielding 1-((6-ethynylpyridin-3-yl)methyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one (68 mg, 35%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washwashed with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated under reduced pressure
  5. customThe residue was purified in a manifold (vac.)
  6. customThe fractions were collected
  7. customevaporated
  8. customThe residue thus obtained
  9. customwas triturated with diisopropyl ether
  10. filtrationThe precipitated solid was filtered off
  11. customdried
  12. customFurther purification by circular chromatography-TLC CH2Cl2/MeOH(NH3)sat

Sources & evidence

ORD record
ord-053d69ad8d6b4cfeb7b543badd84407d
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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