Acetic Anhydride → HCID 71293873, compound

HRID 1747522Notes

Reaction equation

HRID 1747522 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:13])[C:9]([F:12])([F:11])[F:10])[CH:5]=[N:6][CH:7]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15]>N1C=CC=CC=1>[C:14]([O:13][CH:8]([C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[C:9]([F:10])([F:11])[F:12])(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 667978811-(5-Bromopyridin-3-yl)-2,2,2-trifluoroethan-1-ol

Product 1

HCID 71293873HCID 71293873, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In pyridine (2.0 mL) was dissolved 1-(5-bromopyridin-3-yl)-2,2,2-trifluoroethanol (390 mg, 1.52 mmol) obtained in Step 2. Acetic anhydride (2.0 mL) was added and the mixture was stirred at room temperature for 18 hours. The solvent was evaporated under reduced pressure and a saturated aqueous sodium bicarbonate solution and water were added. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) and further purified by preparative thin-layer chromatography (hexane/ethyl acetate=4/1) to give 1-(5-bromopyridin-3-yl)-2,2,2-trifluoroethyl acetate (429 mg, 95% yield).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additiona saturated aqueous sodium bicarbonate solution and water were added
  3. extractionExtraction with ethyl acetate
  4. washwashing with saturated brine
  5. dry with materialdrying over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent in the filtrate was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)
  9. customfurther purified by preparative thin-layer chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-c881178c4d104856a10d03f411c8f1f7
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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