HCID 57974723, compound → HCID 57974724, compound

HRID 1864724Notes

Reaction equation

HRID 1864724 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[CH2:7][N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)([O-])=O>[Pd].C(O)C>[N:16]1[CH:17]=[CH:18][C:13]([C:9]2[N:8]([CH2:7][C:6]3[CH:5]=[C:4]([NH2:1])[CH:21]=[CH:20][CH:19]=3)[CH:12]=[CH:11][N:10]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 57974723HCID 57974723, compound

Product 1

HCID 57974724HCID 57974724, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethanol (20 mL) is added to 4-[1-(3-Nitro-benzyl)-1H-imidazol-2-yl]-pyridine (730 mg, 2.6 mmol) and 10% palladium on charcoal (100 mg) under an atmosphere of argon. The atmosphere is purged 3 times with H2 on a Parr shaker type hydrogenation apparatus, and the mixture is shaken for 4 h at 50 psi H2. The mixture is filtered through celite, and the filter pad is washed with DCM and MeOH (1:1). The solution was concentrated under reduced pressure to afford 3-(2-Pyridin-4-yl-imidazol-1-ylmethyl)-phenylamine as an off-white solid.

Workup

  1. customThe atmosphere is purged 3 times with H2 on a Parr shaker type hydrogenation apparatus
  2. filtrationThe mixture is filtered through celite
  3. washthe filter pad is washed with DCM and MeOH (1:1)
  4. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4c2400adcb1243b7864cd583eeaf5b90
Source dataset
uspto-grants-2009_12
Patent number
US07625931B2

Reaction notes

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