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

HRID 432001Notes

Reaction equation

HRID 432001 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 (1.37g) 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-00b2cad01a234d5f8a6cedebc4c801b5
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

Loading…