tert-Butanol → HCID 178477271, compound

HRID 533651Notes

Reaction equation

HRID 533651 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][C:9](=O)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:16][CH2:17][CH3:18])=[CH:6][C:5]([C:20]([F:23])([F:22])[F:21])=[CH:4][N:3]=1.C(O)(C)(C)C.[H-].[Na+]>C1COCC1>[CH2:17]([S:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:9]1[NH:1][C:2]2=[N:3][CH:4]=[C:5]([C:20]([F:23])([F:22])[F:21])[CH:6]=[C:7]2[N:8]=1)[CH3:18]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 24758Sodium hydride3×HCID 67981470HCID 67981470, compound

Product 1

HCID 178477271HCID 178477271, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of N-(2-amino-5-trifluoromethylpyridine-3-yl)-2-ethylsulfanyl-benzamide (200 mg), tert-butylalcohol (1 ml), and THF (9 ml) was stirred with heating at 80° C., then 60% of sodium hydride (in oil, 56 mg) was added thereto. The mixture was stirred with heating at 80° C. for 2 hours, and then 60% of sodium hydride (in oil, 56 mg) was added. The mixture was further stirred with heating at the same temperature for 2 hours, and then to the mixture, 60% of sodium hydride (in oil, 56 mg) was added, and stirred with heating at the same temperature for 2 hours. The reaction mixture was cooled to room temperature, and evaporated to remove the solvent, and then to the mixture, saturated ammonium chloride solution was added, 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 132 mg of 2-(2-ethylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, Present Compound 351).

Workup

  1. stirringThe mixture was stirred
  2. temperaturewith heating at 80° C. for 2 hours
  3. stirringThe mixture was further stirred
  4. temperaturewith heating at the same temperature for 2 hours
  5. stirringstirred
  6. temperaturewith heating at the same temperature for 2 hours
  7. temperatureThe reaction mixture was cooled to room temperature
  8. customevaporated
  9. customto remove the solvent
  10. additionto the mixture, saturated ammonium chloride solution was added
  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-e52f9413707140adaed0b4cb1ee9829c
Source dataset
uspto-grants-2014_10
Patent number
US08853238B2

Reaction notes

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