Dimethylformamide → HCID 86725168, compound

HRID 1477289Notes

Reaction equation

HRID 1477289 reaction equation
Cl[C:2]1[C:3]([C:12]2[N:24]([CH3:25])[C:15]3=[N:16][CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=[C:14]3[N:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.CN(C=O)C.[CH2:31]([S-:33])[CH3:32].[Na+]>O>[CH2:31]([S:33][C:2]1[C:3]([C:12]2[N:24]([CH3:25])[C:15]3=[N:16][CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=[C:14]3[N:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1)[CH3:32]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 4459711Sodium ethanethiolateHCID 86725169HCID 86725169, compound

Product 1

HCID 86725168HCID 86725168, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-(3-chloro-5-trifluoromethylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.71 g) and DMF (4 ml) was added sodium ethanethiolate (0.24 g) while ice-cooling, and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 2-(3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.76 g), which is hereinafter referred to as “the present compound 4”.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c0a30afc876a46559058ebbaa5c4bf66
Source dataset
uspto-grants-2016_08
Patent number
US09403771B2

Reaction notes

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