Pyridine → 2-(2-ethylsulfanylphenyl)-1-methyl-5-trifluoromethyl-1H-imidazo[4,5-b]pyridine

HRID 533635

Reaction equation

HRID 533635 reaction equation
[CH3:1][NH:2][C:3]1[C:4]([NH2:13])=[N:5][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:8]=1.[CH2:14]([S:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19](O)=O)[CH3:15].CCN=C=NCCCN(C)C.N1C=CC=CC=1>O>[CH2:14]([S:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]1[N:2]([CH3:1])[C:3]2[C:4]([N:13]=1)=[N:5][C:6]([C:9]([F:12])([F:10])[F:11])=[CH:7][CH:8]=2)[CH3:15]

Participants

6

Reactant 4

HCID 1049PyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 4257582-(Ethylsulfanyl)benzoic acidHCID 68091240N3-Methyl-6-(trifluoromethyl)pyridine-2,3-diamine

Product 1

HCID 680912362-(2-ethylsulfanylphenyl)-1-methyl-5-trifluoromethyl-1H-imidazo[4,5-b]pyridineYield 49.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N3-methyl-6-trifluoromethylpyridin-2,3-diamine (0.38 g), 2-ethylsulfanylbenzoic acid (0.40 g), WSC (0.42 g), and pyridine (3 ml) was stirred under reflux for hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. To the resulting residue, tripotassium phosphate (1.06 g) and 1-propanol (4 ml) were added, and stirred under reflux for 4 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.33 g of 2-(2-ethylsulfanylphenyl)-1-methyl-5-trifluoromethyl-1H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 166).

Workup

  1. temperatureunder reflux for hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionTo the resulting residue, tripotassium phosphate (1.06 g) and 1-propanol (4 ml) were added
  6. stirringstirred
  7. temperatureunder reflux for 4 hours
  8. temperatureInto the reaction mixture cooled to room temperature
  9. additionwater was poured
  10. extractionextracted with ethyl acetate
  11. dry with materialThe organic layer was dried over sodium sulfate
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5dede9dd838a454eae773d5607a76f21
Source dataset
uspto-grants-2014_10
Patent number
US08853238B2

Linked notes

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