Methanol → 2-(2-ethylsulfinylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine

HRID 923737Notes

Reaction equation

HRID 923737 reaction equation
[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:22]([CH3:23])[C:13]2=[N:14][CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=[C:12]2[N:11]=1)[CH3:2].I([O-])(=O)(=O)=[O:25].[Na+].CO>O.C1COCC1>[CH2:1]([S:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:22]([CH3:23])[C:13]2=[N:14][CH:15]=[C:16]([C:18]([F:21])([F:19])[F:20])[CH:17]=[C:12]2[N:11]=1)=[O:25])[CH3:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 23667635Sodium periodateHCID 867081912-(2-ethylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 867081922-(2-ethylsulfinylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridineYield 76.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-(2-ethylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.25 g), sodium periodate (0.24 g), methanol (6 ml), water (2 ml), and THF (0.8 ml) was stirred at roam temperature for 20 minutes, and then heated to 50° C., and stirred with heating for further 1.5 hours. To the ice-cooled reaction mixture, water was added. The precipitated crystal was collected by filtration. The obtained crystal was dissolved in ethyl acetate, and washed with saturated aqueous sodium thiosulfate solution, saturated aqueous sodium hydrogen carbonate solution, then saturated brine, sequentially. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was washed with hexane to give 0.20 g of 2-(2-ethylsulfinylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 5).

Workup

  1. stirringstirred
  2. temperaturewith heating for further 1.5 hours
  3. additionwas added
  4. filtrationThe precipitated crystal was collected by filtration
  5. dissolutionThe obtained crystal was dissolved in ethyl acetate
  6. washwashed with saturated aqueous sodium thiosulfate solution, saturated aqueous sodium hydrogen carbonate solution
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. washThe resulting residue was washed with hexane

Sources & evidence

ORD record
ord-19ee2d0d485c42b8b6906ed6b5f4eddf
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

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