8-(Tert-butyldimethylsilyloxy)-2-(6-cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline → 2-(6-Cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-ol

HRID 876445Notes

Reaction equation

HRID 876445 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]=[C:25]([CH:28]4[CH2:30][CH2:29]4)[CH:26]=[CH:27][C:22]3=[N:21][N:20]=1)[CH:15]=[CH:14]2)(C(C)(C)C)(C)C>C1COCC1.[NH4+].[Cl-].O>[CH:28]1([C:25]2[CH:26]=[CH:27][C:22]3[N:23]([C:19]([C:16]4[CH:15]=[CH:14][C:13]5[C:18](=[C:9]([OH:8])[CH:10]=[CH:11][CH:12]=5)[N:17]=4)=[N:20][N:21]=3)[CH:24]=2)[CH2:30][CH2:29]1

Participants

5

Reactant 1

HCID 672305218-(Tert-butyldimethylsilyloxy)-2-(6-cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline

Product 1

HCID 1363378082-(6-Cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-olYield 62.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a 0° C. solution of 8-(tert-butyldimethylsilyloxy)-2-(6-cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline (0.159 g, 0.382 mmol) in 4 mL THF was added solid TBAF hydrate (0.150 g, 0.573 mmol), causing the reaction mixture to turn cloudy. The reaction mixture was warmed to ambient temperature after 5 minutes and then stirred 17 hours, after which it was diluted with saturated NH4Cl and water, causing solids to form. The solids were isolated by vacuum filtration through a Buchner funnel, rinsed with water, and air dried in vacuo to give the title compound (0.072 g, 0.238 mmol, 62.4% yield) as a light pink powder.

Workup

  1. customto form
  2. customThe solids were isolated by vacuum filtration through a Buchner funnel
  3. washrinsed with water, and air
  4. customdried in vacuo

Sources & evidence

ORD record
ord-60ee98cd2fff42f89916d44f7f9f532e
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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