4-(Bromomethyl)benzonitrile → 4-[5-(5-chloro-2-oxo-2H-[1,2']bipyridinyl-5'-ylmethyl)-imidazol-1-ylmethyl]-benzonitrile

HRID 1585887Notes

Reaction equation

HRID 1585887 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1)#[N:2].[Cl:11][C:12]1[CH:13]=[CH:14][C:15](=[O:49])[N:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]3[N:26]=[CH:27][N:28](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:29]=3)=[CH:20][N:19]=2)[CH:17]=1>CC#N>[Cl:11][C:12]1[CH:13]=[CH:14][C:15](=[O:49])[N:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]3[N:26]([CH2:7][C:6]4[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=4)[CH:27]=[N:28][CH:29]=3)=[CH:20][N:19]=2)[CH:17]=1

Participants

4

Reactant 2

HCID 869964-(Bromomethyl)benzonitrileHCID 702869365-chloro-5'-(1-trityl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one

Product 1

HCID 187797164-[5-(5-chloro-2-oxo-2H-[1,2']bipyridinyl-5'-ylmethyl)-imidazol-1-ylmethyl]-benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Cyanobenzyl bromide (0.159 g, 0.813 mmol) and the imidazole from step 5 (0.430 g, 0.813 mmol) in CH3CN (4 mL) were heated at 60° C. for 18 hrs. The reaction was cooled to room temperature and the solvent evaporated in vacuo The residue was suspended in methanol (10 mL) and heated at reflux for 1 hr, cooled and the solvent evaporated in vacuo. The residue was partitioned between sat. NaHCO3 and CH2Cl2 and extracted with CH2Cl2. The organic extracts were dried (MgSO4) and evaporated in vacuo. The residue was chromatographed (silica gel, MeOH: CH2Cl2 3:97 to 4:96 gradient elution) to afford the free base which was converted to the hydrochloride salt to afford the title compound as a white solid.

Workup

  1. customthe solvent evaporated in vacuo The residue
  2. temperatureheated
  3. temperatureat reflux for 1 hr
  4. temperaturecooled
  5. customthe solvent evaporated in vacuo
  6. customThe residue was partitioned between sat. NaHCO3 and CH2Cl2
  7. extractionextracted with CH2Cl2
  8. dry with materialThe organic extracts were dried (MgSO4)
  9. customevaporated in vacuo
  10. customThe residue was chromatographed
  11. wash(silica gel, MeOH: CH2Cl2 3:97 to 4:96 gradient elution)
  12. customto afford the free base which

Sources & evidence

ORD record
ord-02e399558896427cb645e09b3048346b
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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