HCID 178418361, compound → HCID 178437186, compound

HRID 1174676Notes

Reaction equation

HRID 1174676 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:17]=2[N:16]=[CH:15][CH:14]=[CH:13]3)=[CH2:7])[N:3]=[CH:2]1.[H][H]>FC(F)(F)C(O)=O.[Pd]>[NH:1]1[CH:5]=[C:4]([CH:6]([C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:17]=2[N:16]=[CH:15][CH:14]=[CH:13]3)[CH3:7])[N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178437185HCID 178437185, compound

Product 1

HCID 178437186HCID 178437186, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6422Trifluoroacetic acidSolvent2×

Procedure

The vinyl compound, 8-[1-(1H-imidazol-4-yl)-vinyl]-quinoline (0.23 g) in trifluoroacetic acid: TFA (15 mL) was reduced by the action of 10% Pd/C (58 mg) under 50 psi of hydrogen for 18 h at rt. The mixture was filtered through Celite and basified with NH3-MeOH. The solvent was removed under vacuum. The residue was purified by chromatography on silica gel with 4% NH3-MeOH: CH2Cl2 to give 8-[1-(1H-imidazol-4-yl)-ethyl]-quinoline (Intermediate C2) 0.2 g.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customThe solvent was removed under vacuum
  3. customThe residue was purified by chromatography on silica gel with 4% NH3-MeOH

Sources & evidence

ORD record
ord-dd8bebc75dfe48ac8dd21d5bf4802cfd
Source dataset
uspto-grants-2010_11
Patent number
US07838545B2

Reaction notes

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