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

HRID 1421707Notes

Reaction equation

HRID 1421707 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-0f9ad02a9bd94dbdbce19567b9b5a1ec
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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