Pyridine → pentafluorophenyl 5-[(E)-3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoate

HRID 1019055Notes

Reaction equation

HRID 1019055 reaction equation
F[C:2](F)(F)[C:3]([O:5][C:6]1[C:11]([F:12])=[C:10]([F:13])[C:9]([F:14])=[C:8]([F:15])[C:7]=1[F:16])=[O:4].[N:19]1([CH2:24][CH:25]=[CH:26][C:27]2[CH:28]=[CH:29][C:30]([CH2:36][CH2:37][C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=3)=[C:31]([CH:35]=2)[C:32]([OH:34])=[O:33])[CH:23]=[CH:22][N:21]=[CH:20]1.N1C=CC=CC=1>CN(C=O)C>[N:19]1([CH2:24]/[CH:25]=[CH:26]/[C:27]2[CH:35]=[CH:31][C:30]([CH2:36][CH2:37][C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=3)=[C:2]([CH:28]=2)[C:3]([O:5][C:6]2[C:11]([F:12])=[C:10]([F:13])[C:9]([F:14])=[C:8]([F:15])[C:7]=2[F:16])=[O:4])[CH:23]=[CH:22][N:21]=[CH:20]1.[N:19]1([CH2:24]/[CH:25]=[CH:26]\[C:27]2[CH:28]=[CH:29][C:30]([CH2:36][CH2:37][C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=3)=[C:31]([CH:35]=2)[C:32]([O:34][C:6]2[C:7]([F:16])=[C:8]([F:15])[C:9]([F:14])=[C:10]([F:13])[C:11]=2[F:12])=[O:33])[CH:23]=[CH:22][N:21]=[CH:20]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 545106535-[3-(Imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoic acid

Product 2

HCID 18399494pentafluorophenyl 5-[(E)-3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoateHCID 86758617pentafluorophenyl 5-[(Z)-3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Pentafluorophenyl trifluoroacetate (1.47 ml; 8.6 mmol) was added to a solution of 5-[3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoic acid (2.5 g, 7.14 mmol) and pyridine (0.7 ml; 8.6 mmol) in DMF (7 ml). After stirring at ambient temperature overnight, the mixture was evaporated to dryness and the residue extracted with ethyl acetate, washed with saturated sodium hydrogen carbonate and saturated sodium chloride. After evaporation the reaction mixture was purified by flash chromatography eluting with dichloromethane/ethanol (99/1) to give E isomer pentafluorophenyl 5-[(E)-3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoate and Z isomer pentafluorophenyl 5-[(Z)-3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoate. Yield: 68%

Workup

  1. customthe mixture was evaporated to dryness
  2. extractionthe residue extracted with ethyl acetate
  3. washwashed with saturated sodium hydrogen carbonate and saturated sodium chloride
  4. customAfter evaporation the reaction mixture
  5. customwas purified by flash chromatography
  6. washeluting with dichloromethane/ethanol (99/1)

Sources & evidence

ORD record
ord-ef4663cab2784bf281983517d7957d8b
Source dataset
uspto-grants-2002_11
Patent number
US06486156B1

Reaction notes

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