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

HRID 887345

Reaction equation

HRID 887345 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

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 6344DichloromethaneSolvent

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-bdf6ae3cd782445b8a33541a946cf72b
Source dataset
uspto-grants-2012_08
Patent number
US08247421B2

Linked notes

Loading…