Trityl chloride → 4-(2-bromophenyl)-1-trityl-1H-imidazole

HRID 2105024Notes

Reaction equation

HRID 2105024 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[CH:10][NH:11][CH:12]=1.[C:13](Cl)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[CH:10][N:11]([C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:12]=1

Participants

5

Reactant 2

HCID 6456Trityl chlorideHCID 178419371HCID 178419371, compound

Product 1

HCID 221851434-(2-bromophenyl)-1-trityl-1H-imidazoleYield 73.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(2-bromophenyl)-1H-imidazole (880 mg, 3.94 mmol) in 10 mL DMF, were added TEA (0.605 mL, 4.34 mmol) and trityl chloride (1.21 g, 4.34 mmol). The mixture was stirred at rt for 14 h, then diluted with EtOAc. The organic phase was washed with H2O (2×) and brine, dried (Na2SO4), filtered through a 1″ pad of silica gel and concentrated. The crude product was purified by flash chromatography (0 to 40% EtOAc/hexanes gradient) to afford 1.34 g of Intermediate 217.1 as an off-white solid. LCMS (50 to 100% B, 4 min gradient, A 95% H2O/5% CH3CN/0.1% TFA, B=5% H2O/95% CH3CN/0.1% TFA) RT=0.77 min, 465.2 (M+H)+.

Workup

  1. washThe organic phase was washed with H2O (2×) and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered through a 1″ pad of silica gel
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography (0 to 40% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-1e65abdbc4824b6abbbd89482cecb176
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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