HCID 21875609, compound → HCID 21876166, compound

HRID 967849Notes

Reaction equation

HRID 967849 reaction equation
[CH2:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][N:16]=[N+]=[N-])=[CH:10][CH:9]=2)[C:6]2[CH:19]=[CH:20][CH:21]=[CH:22][C:5]=2[N:4]=1)[CH3:2]>CO.[Pd]>[CH2:1]([C:3]1[N:7]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][NH2:16])=[CH:12][CH:13]=2)[C:6]2[CH:19]=[CH:20][CH:21]=[CH:22][C:5]=2[N:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 21875609HCID 21875609, compound

Product 1

HCID 21876166HCID 21876166, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-[4-(2-ethyl-1H-benzimidazol-1-yl)phenyl]ethyl azide (990 mg, 3.4 mmol) in methanol (20 mL) was added 10% Pd—C (100 mg). The resulting mixture was stirred for 4 h under hydrogen atmosphere. The mixture was filtered through a pad of Celite and the filtrate was concentrated. The residue was purified by flash column chromatography on silica gel eluting with dichloromethane/methanol/triethylamine (100:5:1) to afford 855 mg (94%) of the title compound as white solids: 1H-NMR (CDCl3)δ1.26 (3H, t, J=7.5 Hz), 2.76 (2H, q, J=7.5 Hz), 2.89 (2H, t, J=6.5 Hz), 3.06 (2H, t, J=6.5 Hz), 7.45-7.06 (7H, m),7.80-7.74 (1H, m).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by flash column chromatography on silica gel eluting with dichloromethane/methanol/triethylamine (100:5:1)

Sources & evidence

ORD record
ord-44d470360bd94aea918f7066cdbd918b
Source dataset
uspto-grants-2005_10
Patent number
US06956050B2

Reaction notes

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