2-methyl-6-[1-(1-trityl-1H-imidazol-4-yl)-vinyl]-pyridine → HCID 178424904, compound

HRID 748649Notes

Reaction equation

HRID 748649 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([C:10]2[N:11]=[CH:12][N:13](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:14]=2)=[CH2:9])[N:3]=1>FC(F)(F)C(O)=O.[Pd]>[NH:13]1[CH:14]=[C:10]([CH:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[N:3]=2)[CH3:9])[N:11]=[CH:12]1

Participants

4

Reactant 1

HCID 597514582-methyl-6-[1-(1-trityl-1H-imidazol-4-yl)-vinyl]-pyridine2×

Product 1

HCID 178424904HCID 178424904, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 2-methyl-6-[1-(1-trityl-1H-imidazol-4-yl)-vinyl]-pyridine (Intermediate D4) (460 mg, 1.1 mmol) in trifluoroacetic acid (TFA) (25 mL) was reduced by the action of 10% Pd/C (100 mg) under H2 at 35 psi for 20 h at rt. The mixture was filtered through Celite and freed of solvent under reduced pressure. The residue was purified by chromatography on silica gel with 5% NH3-MeOH:CH2Cl2 to give 2-[1-(1H-imidazol-4-yl)-ethyl]-6-methyl-pyridine (Intermediate D5) as a solid, 150 mg (93%).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customThe residue was purified by chromatography on silica gel with 5% NH3-MeOH

Sources & evidence

ORD record
ord-f374b20e47a84263b6b3af8dee608fbe
Source dataset
uspto-grants-2008_07
Patent number
US07399868B2

Reaction notes

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