Pyridine → 2-(2-ethylsulfanylphenyl)-3-methyl-5-trifluoromethyl-3H-imidazo[4,5-b]pyridine

HRID 923769Notes

Reaction equation

HRID 923769 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[C:5]([C:10]([F:13])([F:12])[F:11])[N:4]=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=[N:4][C:5]([C:10]([F:11])([F:12])[F:13])=[CH:6][CH:7]=[C:8]2[N:9]=1)[CH3:15]

Participants

6

Reactant 4

HCID 1049PyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 4257582-(Ethylsulfanyl)benzoic acidHCID 68091056N2-Methyl-6-(trifluoromethyl)pyridine-2,3-diamine

Product 1

HCID 680910872-(2-ethylsulfanylphenyl)-3-methyl-5-trifluoromethyl-3H-imidazo[4,5-b]pyridineYield 57.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N2-methyl-6-trifluoromethylpyridin-2,3-diamine (0.96 g), 2-ethylsulfanylbenzoic acid (1.01 g), WSC (1.06 g), and pyridine (5 ml) was stirred under reflux for 3 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, a mixture of tripotassium phosphate (2.65 g) and 1-propanol (10 ml) was 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 0.98 g of 2-(2-ethylsulfanylphenyl)-3-methyl-5-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 151).

Workup

  1. temperatureunder reflux for 3 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, a mixture of tripotassium phosphate (2.65 g) and 1-propanol (10 ml)
  6. additionwas added
  7. stirringstirred
  8. temperatureunder reflux for 4 hours
  9. temperatureInto the reaction mixture cooled to room temperature
  10. additionwater was poured
  11. extractionextracted with ethyl acetate
  12. dry with materialThe organic layer was dried over sodium sulfate
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5c9d5563ece041e7a40ce1b6f66a8255
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

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