HCID 67133050, compound → HCID 67133348, compound

HRID 545326Notes

Reaction equation

HRID 545326 reaction equation
[C:1]([C:7]1[CH:8]=[C:9]([C:13]2[NH:14][CH:15]=[CH:16][N:17]=2)[CH:10]=[CH:11][CH:12]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH3:6]>CO.[Pd]>[CH2:1]([C:7]1[CH:8]=[C:9]([C:13]2[NH:17][CH:16]=[CH:15][N:14]=2)[CH:10]=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 1

HCID 67133050HCID 67133050, compound

Product 1

HCID 67133348HCID 67133348, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 6.15 g (27.4 mmol) of 2-(3-hex-1-ynyl-phenyl)-1H-imidazole in 140 ml of MeOH was treated with 1.46 g (1.4 mmol) of Pd—C (10%) and hydrogenated with H2 (1 bar) at RT for 1 hour. After removal the catalyst by filtration, the solvent was evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 98:2) to give 5.92 g (95%) of the title compound as light brown solid. MS: 229.2 (MH+).

Workup

  1. customAfter removal the catalyst
  2. filtrationby filtration
  3. customthe solvent was evaporated
  4. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 98:2)

Sources & evidence

ORD record
ord-90be0913ea2742fb89d240d6cce68351
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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