Tetrabutylammonium Fluoride → 2-(7-Methyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-ol

HRID 876508Notes

Reaction equation

HRID 876508 reaction equation
[Si]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([C:19]1[N:23]3[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:22]3=[N:21][N:20]=1)[CH:15]=[CH:14]2)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.[Cl-].[NH4+]>[CH3:28][C:26]1[CH:25]=[CH:24][N:23]2[C:19]([C:16]3[CH:15]=[CH:14][C:13]4[C:18](=[C:9]([OH:8])[CH:10]=[CH:11][CH:12]=4)[N:17]=3)=[N:20][N:21]=[C:22]2[CH:27]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 672296368-(Tert-butyldimethylsilyloxy)-2-(7-methyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline

Product 1

HCID 1363378102-(7-Methyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-olYield 99%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 8-(tert-butyldimethylsilyloxy)-2-(7-methyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline (5.00 g, 12.8 mmol) in tetrahydrofuran (100 mL) at 0° C. was added tetrabutylammonium fluoride (19.2 mL, 1 M in tetrahydrofuran, 19.2 mmol). The reaction was stirred for 6 hours at ambient temperature and then diluted with saturated aqueous ammonium chloride. The mixture was concentrated under reduced pressure, triturated with water, filtered and air-dried to provide 3.50 g (99%) of desired product as a white solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customtriturated with water
  3. filtrationfiltered
  4. customair-dried

Sources & evidence

ORD record
ord-4e79d9b9204344b98b3263283d2c1bbe
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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