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

HRID 422279Notes

Reaction equation

HRID 422279 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. 4 mL of trifluoroacetic acid was added at room temperature to the solution. The resulting mixture was stirred at R.T. for 2 h. 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 triturated 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. customThe brownish solid was triturated in a mixture Et2O/Pentane
  8. filtrationThe solid was collected by filtration
  9. washwashed with a mixture Et2O/Pentane
  10. customThe solid was dried by lyophilisation

Sources & evidence

ORD record
ord-91a3b2e9fe0d4efb8b8bc99768ab16c5
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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