8-methyl-7-[1-(1-trityl-1H-imidazol-4-yl)vinyl]quinoline → HCID 178423884, compound

HRID 747262Notes

Reaction equation

HRID 747262 reaction equation
[CH3:1][C:2]1[C:3]([C:12]([C:14]2[N:15]=[CH:16][N:17](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:18]=2)=[CH2:13])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2>C(O)(C(F)(F)F)=O.[Pd]>[NH:17]1[CH:18]=[C:14]([CH:12]([C:3]2[C:2]([CH3:1])=[C:11]3[C:6]([CH:7]=[CH:8][CH:9]=[N:10]3)=[CH:5][CH:4]=2)[CH3:13])[N:15]=[CH:16]1

Participants

4

Reactant 1

HCID 597495448-methyl-7-[1-(1-trityl-1H-imidazol-4-yl)vinyl]quinoline2×

Product 1

HCID 178423884HCID 178423884, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 8-methyl-7-[1-(1-trityl-1H-imidazol-4-yl)vinyl]quinoline (Intermediate M5) (2.14 g, 4.49 mmol) in TFA (˜40 mL) was reduced by action of 10% Pd/C (0.51 g) under H2 (45-50 psi) for 16 h at rt. The mixture was filtered through celite and the solvent was removed under vacuum. The residue was purified by chromatography on silica gel with 2-4% NH3-MeOH:CH2Cl2 to give 7-[1-(1H-imidazol-4-yl)ethyl]-8-methylquinoline (Intermediate M6) 834 mg, (79%).

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 2-4% NH3-MeOH

Sources & evidence

ORD record
ord-5aef4194ddea4b32a084e6b6ee7e1a48
Source dataset
uspto-grants-2008_07
Patent number
US07396849B2

Reaction notes

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