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

HRID 533609

Reaction equation

HRID 533609 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 3.5 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-349e825d2bba4fcabfbe3ec47462122a
Source dataset
uspto-grants-2014_10
Patent number
US08853238B2

Linked notes

Loading…