Trifluoroacetic acid → HCID 178519870, compound

HRID 1929387Notes

Reaction equation

HRID 1929387 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[C:14]([C:15]([C:17]2[N:18]=[CH:19][N:20](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:21]=2)=[O:16])=[CH:13][CH:12]=[CH:11][N:10]=1>>[F:8][C:9]1[C:14]([C:15]([C:17]2[N:18]=[CH:19][NH:20][CH:21]=2)=[O:16])=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57690843HCID 57690843, compound

Product 1

HCID 178519870HCID 178519870, compoundYield 51.5%

Procedure

Trifluoroacetic acid (5 ml) was added to (2-fluoropyridin-3-yl)(1-trityl-1H-imidazol-4-yl)methanone (1.1 g, 2.54 mmol). The reaction mixture was stirred for 18 hours. The crude mixture was concentrated in vacuo and treated with a 2N aqueous solution of HCl. The aqueous phase was extracted with diethyl ether and basified with NaOH pellets. The compound was extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound (250 mg, 51% yield).

Workup

  1. concentrationThe crude mixture was concentrated in vacuo
  2. additiontreated with a 2N aqueous solution of HCl
  3. extractionThe aqueous phase was extracted with diethyl ether
  4. extractionThe compound was extracted with ethyl acetate
  5. washThe organic phase was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a8fb8c0ae1d4db381c240964ecb8366
Source dataset
uspto-grants-2012_05
Patent number
US08188071B2

Reaction notes

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