2-Bromopyridine → 2-(1-trityl-1H-imidazol-4-yl)pyridine

HRID 2216891Notes

Reaction equation

HRID 2216891 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[N:7]=[CH:8][N:9]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=1)CCC.Br[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:40]1[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=1[C:6]1[N:7]=[CH:8][N:9]([C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:10]=1

Participants

5

Reactant 2

HCID 79732-BromopyridineHCID 118281174-(Tributylstannyl)-1-tritylimidazole

Product 1

HCID 219426882-(1-trityl-1H-imidazol-4-yl)pyridineYield 77.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

The crude 4-tributylstannyl-1-trityl-1H-imidazole (1.37 g) in toluene (10 mL) was treated sequentially with 2-bromopyridine (0.33 mL, 3.43 mmol) and Pd(PPh3)4 (0.26 g, 0.23 mmol). The reaction mixture was heated at reflux under an argon atmosphere for 4 hours. After cooling, the reaction mixture was concentrated in vacuo. The residue was dissolved in chloroform (50 mL) and sequentially washed with aqueous saturated potassium fluoride (75 mL), water (75 mL) and brine (100 mL). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated in-vacuo to afford 0.69 g of crude 4-(2-pyridyl)-1-trityl-1H-imidazole.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under an argon atmosphere for 4 hours
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated in vacuo
  5. dissolutionThe residue was dissolved in chloroform (50 mL)
  6. washsequentially washed with aqueous saturated potassium fluoride (75 mL), water (75 mL) and brine (100 mL)
  7. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-5450ae1afaa74ac694af3e35d28c3907
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

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