methyl 4-[(Z)-3-(imidazol-1-yl)-2-(thiazol-2-yl)-prop-1-enyl]-2-phenyl-benzoate → Methyl 4-[3-(imidazol-1-yl)-2-(thiazol-2-yl)-propyl]-2-phenyl-benzoate

HRID 2227995Notes

Reaction equation

HRID 2227995 reaction equation
[N:1]1([CH2:6]/[C:7](/[C:25]2[S:26][CH:27]=[CH:28][N:29]=2)=[CH:8]/[C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:10]=2)[CH:5]=[CH:4][N:3]=[CH:2]1>CO.[Pd]>[N:1]1([CH2:6][CH:7]([C:25]2[S:26][CH:27]=[CH:28][N:29]=2)[CH2:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:10]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 1

HCID 70030731methyl 4-[(Z)-3-(imidazol-1-yl)-2-(thiazol-2-yl)-prop-1-enyl]-2-phenyl-benzoate

Product 1

HCID 18474622Methyl 4-[3-(imidazol-1-yl)-2-(thiazol-2-yl)-propyl]-2-phenyl-benzoateYield 25%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of methyl 4-[(Z)-3-(imidazol-1-yl)-2-(thiazol-2-yl)-prop-1-enyl]-2-phenyl-benzoate (see this Example, compound a), step B) (1.2 g; 3 mmol) and 10% Pd/C (0.3 g) in MeOH (10 ml) was hydrogenated for 6 hours. After filtration of the catalyst and evaporation to dryness the residue was purified by flash chromatography eluting with CH2Cl2/EtOH (98/2) to give methyl 4-[3-(imidazol-1-yl)-2-(thiazol-2-yl)-propyl]-2-phenyl-benzoate. Yield=25%.

Workup

  1. filtrationAfter filtration of the catalyst and evaporation to dryness the residue
  2. customwas purified by flash chromatography
  3. washeluting with CH2Cl2/EtOH (98/2)

Sources & evidence

ORD record
ord-a162a0e873884e29815da4411c0ce315
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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