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Pentafluorophenol → 2-(perfluorophenoxy)-4-(1-tosyl-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile

HRID 40843
Notes
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Reaction equation

HRID 40843 reaction equation
CS[C:3]1[N:8]=[C:7]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:16]=3)[N:11]([S:22]([C:25]3[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=3)(=[O:24])=[O:23])[CH:10]=2)[C:6]([C:32]#[N:33])=[CH:5][N:4]=1.ClC1C=CC=C(C(OO)=O)C=1.[F:45][C:46]1[C:51]([OH:52])=[C:50]([F:53])[C:49]([F:54])=[C:48]([F:55])[C:47]=1[F:56]>ClCCl>[F:45][C:46]1[C:47]([F:56])=[C:48]([F:55])[C:49]([F:54])=[C:50]([F:53])[C:51]=1[O:52][C:3]1[N:8]=[C:7]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]([F:19])([F:20])[F:21])[CH:16]=3)[N:11]([S:22]([C:25]3[CH:26]=[CH:27][C:28]([CH3:29])=[CH:30][CH:31]=3)(=[O:24])=[O:23])[CH:10]=2)[C:6]([C:32]#[N:33])=[CH:5][N:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 13041PentafluorophenolHCID 70297m-Chloroperbenzoic acidHCID 594145372-(Methylthio)-4-(1-tosyl-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile

Product 1

HCID 594143782-(perfluorophenoxy)-4-(1-tosyl-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrileYield 31%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

2-(Methylthio)-4-(1-tosyl-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile (150 mg, 0.31 mmol) was dissolved in dichloromethane at room temperature. Meta-chloroperbenzoic acid (110 mg, 0.64 mmol) was added in one portion and the reaction was stirred for 5 minutes. Pentafluorophenol (285 mg, 1.55 mmol) was added and the solution was stirred at room temperature for 3 hours. The crude mixture was washed with a diluted solution of sodium bicarbonate and brine. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography to afford the title compound as a solid (60 mg, 31% yield).

Workup

  1. stirringthe solution was stirred at room temperature for 3 hours
  2. washThe crude mixture was washed with a diluted solution of sodium bicarbonate and brine
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on silica gel by flash column chromatography

Sources & evidence

ORD record
ord-998258ca017c4116b9667045a1ff24a8
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08530489B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes