Sodium Carbonate → 5-Chloro-2-(4-fluorophenyl)-1-(2-methylsulfinyl-4-pyrimidinyl)imdazo[4,5-b]pyridine

HRID 396371

Reaction equation

HRID 396371 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]=[C:9]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[N:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=3)[C:5]2=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:34])C=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.CC(O)=O>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]=[C:9]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[N:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17]([CH3:18])=[O:34])[N:12]=3)[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 224861505-Chloro-2-(4-fluorophenyl)-1-(2-methylthio-4-pyrimidinyl)imidazo[4,5-b]pyridine

Product 1

HCID 224861275-Chloro-2-(4-fluorophenyl)-1-(2-methylsulfinyl-4-pyrimidinyl)imdazo[4,5-b]pyridineYield 103.1%

Reagents, catalysts & solvents 1

HCID 21922555Acetic acid methylene chlorideSolvent

Procedure

5-Chloro-2-(4-fluorophenyl)-1-(2-methylthio-4-pyrimidinyl)imidazo[4,5-b]pyridine (372 mg 1 mmol) is dissolved in CH2Cl2/HOAc (7 ml 5/2) and treated with MCPBA (270 mg 70% 1.1 mmol) at 0° C. for 30 min. The reaction mixture is poured on 2N Na2CO3 and extracted with ethyl acetate three times. The combined organic phases are dried over Na2SO4, filtered, evaporated to dryness and purified by SiO2 chromatography (ethyl acetate) to yield the title compound (400 mg 100%) as yellow foam.

Workup

  1. extractionextracted with ethyl acetate three times
  2. dry with materialThe combined organic phases are dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. custompurified by SiO2 chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-75eef910ccef439f8b5bda06d552cd72
Source dataset
uspto-grants-2003_08
Patent number
US06608072B1

Linked notes

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