Tetrabutylammonium Fluoride → HCID 136337804, compound

HRID 876384Notes

Reaction equation

HRID 876384 reaction equation
[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:20][Si](C(C)(C)C)(C)C)[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([OH:20])[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 672314422-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-8-(tert-butyldimethylsilyloxy) quinoline

Product 1

HCID 136337804HCID 136337804, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-(tert-butyldimethylsilyloxy)quinoline (18.92 g, 50.25 mmol) in anhydrous THF (400 mL) at 0° C. was added tetrabutylammonium fluoride (75.4 mL, 1.0 M/THF, 75.4 mmol). After stirring for 1 hour at this temperature the mixture was partitioned between saturated NaHCO3 and EtOAc. The aqueous phase was extracted with EtOAc and the combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was triturated with CH2Cl2, filtered and dried in vacuo to provide 11.91 g (90%) of desired product as a beige solid.

Workup

  1. customwas partitioned between saturated NaHCO3 and EtOAc
  2. extractionThe aqueous phase was extracted with EtOAc
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated with CH2Cl2
  8. filtrationfiltered
  9. customdried in vacuo

Sources & evidence

ORD record
ord-db9ad30d7d244cb78eb6a54852a4f876
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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