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Tetrahydrofuran → 2-(6-Fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-ol

HRID 2035604
Notes
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Reaction equation

HRID 2035604 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]([F:28])[CH:26]=[CH:27][C:22]3=[N:21][N:20]=1)[CH:15]=[CH:14]2)(C(C)(C)C)(C)C.C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C([O-])(O)=O.[Na+]>CCOC(C)=O.O>[F:28][C:25]1[CH:26]=[CH:27][C:22]2[N:23]([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]=2)[CH:24]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 672311328-(Tert-butyldimethylsilyloxy)-2-(6-fluoro[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline

Product 1

HCID 1363378062-(6-Fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-olYield 9%

Reagents, catalysts & solvents

2
HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 8-(tert-butyldimethylsilyloxy)-2-(6-fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline (560 mg, 1.4195 mmol) in THF (10.13 mL, 1.267 mmol) was cooled to 0° C. in an ice bath. TBAF (1M in THF, 2.122 mL, 2.129 mmol) was added by syringe and the mixture stirred for 1 hour at 0° C. Water was added, followed by saturated aqueous NaHCO3 solution. The mixture was transferred to a separatory funnel, diluting with EtOAc and water. The mixture was extracted with EtOAc, the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography eluting with 10-15% MeOH 1% NH4OH in EtOAc to give the product as a yellow film (35 mg, 9% yield). MS APCI (+) m/z 281.2 (M+1) detected.

Workup

  1. customThe mixture was transferred to a separatory funnel
  2. extractionThe mixture was extracted with EtOAc
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography
  8. washeluting with 10-15% MeOH 1% NH4OH in EtOAc
  9. customto give the product as a yellow film (35 mg, 9% yield)

Sources & evidence

ORD record
ord-d614a9ee788f486a9366e33d5461bdef
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08575145B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes