2-Iodoxybenzoic acid → HCID 86714755, compound

HRID 2171870Notes

Reaction equation

HRID 2171870 reaction equation
[F:1][C:2]1[C:3]([NH:28][CH:29]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:30][CH2:31][OH:32])=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[N:10]([S:18]([C:21]3[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:9]=2)=[N:6][CH:7]=1.I(C1C=CC=CC=1C(O)=O)(=O)=O>C1COCC1>[F:1][C:2]1[C:3]([NH:28][CH:29]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:30][CH:31]=[O:32])=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[N:10]([S:18]([C:21]3[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=3)(=[O:19])=[O:20])[CH:9]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 1087942-Iodoxybenzoic acidHCID 71247355HCID 71247355, compound2×

Product 1

HCID 86714755HCID 86714755, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of racemic 3-((5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)amino)-4,4-dimethylpentan-1-ol, 82a, (1.60 g, 3.10 mmol) in THF (64 mL) was added 2-iodoxybenzoic acid (Ibx) (3.86 g, 6.21 mmol). The reaction mixture was heated to reflux under at atmosphere of nitrogen for 30 minutes. After cooling the mixture to room temperature, the solids were filtered. An aqueous saturated NaHCO3 solution was added to the filtrate and the biphasic mixture was stirred for 30 minutes. The mixture was further diluted with dichloromethane and the phases separated. The aqueous layer was extracted again with dichloromethane. The combined organic phases were dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was purified via silica gel chromatography (EtOAc/Hexanes) to afford 1.59 g of the desired product

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under at atmosphere of nitrogen for 30 minutes
  3. filtrationthe solids were filtered
  4. additionAn aqueous saturated NaHCO3 solution was added to the filtrate
  5. additionThe mixture was further diluted with dichloromethane
  6. customthe phases separated
  7. extractionThe aqueous layer was extracted again with dichloromethane
  8. dry with materialThe combined organic phases were dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe resulting residue was purified via silica gel chromatography (EtOAc/Hexanes)

Sources & evidence

ORD record
ord-fcb85690f2f249a4b709e0af956a3b1a
Source dataset
uspto-grants-2015_06
Patent number
US09051319B2

Reaction notes

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