Trifluoroacetic acid → N-(4-Fluorophenyl)-5-(2-pyridinyl)-4-pentynamide

HRID 1189077Notes

Reaction equation

HRID 1189077 reaction equation
C(OC(=O)[N:7]([C:15](=[O:26])[CH2:16][CH2:17][C:18]#[C:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.O>[F:14][C:11]1[CH:12]=[CH:13][C:8]([NH:7][C:15](=[O:26])[CH2:16][CH2:17][C:18]#[C:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66598279HCID 66598279, compound

Product 1

HCID 11615961N-(4-Fluorophenyl)-5-(2-pyridinyl)-4-pentynamideYield 83.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl-5-(pyridin-2-yl)pent-4-ynoyl-4-fluorophenylcarbamate (299 mg, 0.81 mmol) was dissolved in DCM (4 mL) with 0.01% w/w of water. 4mL of trifluoroacetic acid was added at room temperature to the solution. The resulting mixture was stirred at R.T. for 2h. The solvent was removed under reduced pressure. The brown oil was dissolved in saturated NaHCO3 until pH=8. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4 and the solvent was removed under reduced pressure. The brownish solid was tritureted in a mixture Et2O/Pentane:50/50. The solid was collected by filtration and washed with a mixture Et2O/Pentane:50/50. The solid was dried by lyophilisation to afford 181 mg of N-(4-fluorophenyl)-5-(pyridine-2-yl)pent-4-ynamide (Yield: 83%) as a colorless solid (M.P.=189.9-190.2° C.).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe brown oil was dissolved in saturated NaHCO3 until pH=8
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. customthe solvent was removed under reduced pressure
  7. filtrationThe solid was collected by filtration
  8. washwashed with a mixture Et2O/Pentane
  9. customThe solid was dried by lyophilisation

Sources & evidence

ORD record
ord-be8ef2e0a725451ebf5f9873037573f2
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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