tert-Butyl mercaptan → 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine

HRID 923742Notes

Reaction equation

HRID 923742 reaction equation
[CH3:1][C:2]([SH:5])([CH3:4])[CH3:3].[H-].[Na+].F[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:27]([CH3:28])[C:18]2=[N:19][CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=[C:17]2[N:16]=1.C(=O)([O-])O.[Na+]>CN(C=O)C>[C:2]([S:5][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:27]([CH3:28])[C:18]2=[N:19][CH:20]=[C:21]([C:23]([F:26])([F:24])[F:25])[CH:22]=[C:17]2[N:16]=1)([CH3:4])([CH3:3])[CH3:1]

Participants

6

Reactant 4

HCID 6387tert-Butyl mercaptanHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 679818402-(2-fluorophenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 867081972-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridineYield 88.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of tert-butylthiol (0.67 g) and DMF (12 ml), sodium hydride (60% in oil) was added under ice-cooling. The mixture was stirred under ice-cooling for 10 minutes, and then 2-(2-fluorophenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (1.09 g) was added. The mixture was stirred at room temperature for 1 hour, and then stirred with heating at 60° C. for 1.5 hours, then at 80° C. for 2 hours. Into the reaction mixture cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 1.19 g of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 15).

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. temperaturecooling for 10 minutes
  4. stirringThe mixture was stirred at room temperature for 1 hour
  5. stirringstirred
  6. temperatureInto the reaction mixture cooled to room temperature
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7438adcfe07a437fbd875130dffee463
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

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