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

HRID 923749Notes

Reaction equation

HRID 923749 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[S:17][CH2:18][CH3:19])[N:8]([CH3:20])[C:5]2=[N:6][CH:7]=1.I([O-])(=O)(=O)=[O:22].[Na+].CO>O.C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[S:17]([CH2:18][CH3:19])=[O:22])[N:8]([CH3:20])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 23667635Sodium periodateHCID 679820336-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 867082046-bromo-2-(2-ethylsulfinylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridineYield 90.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (0.20 g), sodium periodate (0.18 g), methanol (3 ml), water (1 ml), and THF (0.4 ml) was stirred at room temperature for 3.3 hours. Water was poured thereinto under ice-cooling, and then the precipitated solid was collected by filtration. The obtained solid was washed with water and hexane, and dried to give 0.19 g of 6-bromo-2-(2-ethylsulfinylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 43).

Workup

  1. temperatureunder ice-cooling
  2. filtrationthe precipitated solid was collected by filtration
  3. washThe obtained solid was washed with water and hexane
  4. customdried

Sources & evidence

ORD record
ord-2a14d5278174428f9e4f5ff7a19ed98c
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

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