1,1-Dibromoethane → 1-Trityl-4-(4-cyanobenzyl)5-methylimidazole

HRID 1422340Notes

Reaction equation

HRID 1422340 reaction equation
Br[CH:2](Br)[CH3:3].[CH:5]1[C:10]([CH2:11]Br)=[CH:9][CH:8]=[C:7]([C:13]#[N:14])[CH:6]=1.IC1[N:20]([C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:19]=[N:18][CH:17]=1>C1COCC1.[Zn]>[C:21]([N:20]1[C:2]([CH3:3])=[C:17]([CH2:11][C:10]2[CH:9]=[CH:8][C:7]([C:13]#[N:14])=[CH:6][CH:5]=2)[N:18]=[CH:19]1)([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 112011,1-DibromoethaneHCID 869964-(Bromomethyl)benzonitrileHCID 154285835-iodo-1-trityl-1H-imidazole

Product 1

HCID 187791611-Trityl-4-(4-cyanobenzyl)5-methylimidazole

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

To a suspension of activated zinc dust (0.262 g, 3.99 mmol) in THF (1 mL) was added dibromoethane (0.035 mL, 0.039 mmol) and the reaction stirred under argon at 20° C. for 45 minutes. The suspension was cooled to 0° C. and a-bromo-p-tolunitrile (0.51 g, 2.60 mmol) in THF (3 mL) was added dropwise over a period of 10 minutes. The reaction was then allowed to stir at 20° C. for 45 minutes and bis(triphenylphosphine)Nickel II chloride (0.130 g, 0.399 mmol) and 5-iodo-1-trityl imidazole (15.95 g, 36.6 mmol) were added in one portion The resulting mixture was stirred 3 hours at 20° C. and then quenched by addition of saturated NH3 solution (2 mL) and the mixture stirred for 3 hours, extracted with EtOAc (2×25 mL), dried (MgSO4) and the solvent evaporated in vacuo. The residue was chromatographed (Silica gel, 20% EtOAc in CH2Cl2 to afford the title compound as a white solid.

Workup

  1. temperatureThe suspension was cooled to 0° C.
  2. stirringto stir at 20° C. for 45 minutes
  3. stirringwas stirred 3 hours at 20° C.
  4. customquenched by addition of saturated NH3 solution (2 mL)
  5. stirringthe mixture stirred for 3 hours
  6. extractionextracted with EtOAc (2×25 mL)
  7. dry with materialdried (MgSO4)
  8. customthe solvent evaporated in vacuo
  9. customThe residue was chromatographed (Silica gel, 20% EtOAc in CH2Cl2

Sources & evidence

ORD record
ord-1b058e00f27f407593b2adb340464d8f
Source dataset
uspto-grants-2000_06
Patent number
US06080870

Reaction notes

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