Sodium Carbonate → 2-Chloro-5-(pyridin-4-yl)benzaldehyde

HRID 896089Notes

Reaction equation

HRID 896089 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[CH:4][C:3]=1[CH:14](C1C=NC(NC2C=CC(F)=CC=2F)=CC=1)[OH:15].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C([O-])([O-])=O.[Na+].[Na+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=2)=[CH:4][C:3]=1[CH:14]=[O:15]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 22349577(2-Chloro-5-pyridin-4-yl-phenyl)-[6-(2,4-difluoro-phenylamino)-pyridin-3-yl]-methanolHCID 131709961Jones' reagent

Product 1

HCID 223495862-Chloro-5-(pyridin-4-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(2-Chloro-5-pyridin-4-yl-phenyl)-[6-(2,4-difluoro-phenylamino)-pyridin-3-yl]-methanol (111 mg; 0.26 mmol) is dissolved in acetone (20 ml) and treated with Jones reagent (0.45 ml; 1 mmol) for 20 min at room temperature. 2N Na2CO3 is added to the reaction mixture and extracted with ethyl acetate three times. The combined organic phases are dried over Na2SO4 and evaporated to dryness. Purification via chromatography (SiO2; CH2Cl2/MeOH 98/2) provides the title compound as a slightly colored foam (30 mg; 27%).

Workup

  1. extractionextracted with ethyl acetate three times
  2. dry with materialThe combined organic phases are dried over Na2SO4
  3. customevaporated to dryness
  4. customPurification via chromatography (SiO2; CH2Cl2/MeOH 98/2)

Sources & evidence

ORD record
ord-28cb6dbe23a64ffe8c2addc75f15f8b4
Source dataset
uspto-grants-2005_07
Patent number
US06919336B2

Reaction notes

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