Sodium hydride → 4-Bromo-1-{2-(trityloxy)ethyl}-1H-imidazole

HRID 2277498Notes

Reaction equation

HRID 2277498 reaction equation
[Br:1][C:2]1[NH:6][CH:5]=[N:4][CH:3]=1.[H-].[Na+].Br[CH2:10][CH2:11][O:12][C:13]([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.O>[Br:1][C:2]1[N:6]=[CH:5][N:4]([CH2:10][CH2:11][O:12][C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 961251H-Imidazole, 4-bromo-HCID 109595312-Bromoethyl trityl ether

Product 1

HCID 693507044-Bromo-1-{2-(trityloxy)ethyl}-1H-imidazoleYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5-bromo-1H-imidazole as prepared in part A (2.2 g, 15 mmol) in DMF (22 mL) at 0° C. was added NaH (658 mg, 60% dispersion, 2.42 mmol) in small portions. The resulting solution was allowed to warm to r.t. and then stirred for 1 hr. The solution was cooled to 0° C. and 1,1′,1″-[(2-bromoethoxy)methanetriyl]tribenzene (5.5 g, 15 mmol) in DMF (10 mL) was added drop-wise. The resulting solution was allowed to warm to r.t. where stirring continued until the reaction was judged complete by TLC (16 hr). The suspension was diluted with water and extracted with DCM (2×50 mL). The organics were dried (MgSO4), filtered, and concentrated to a solid that was recrystallized (EtOAc/Hex) to give 4.47 g of the title compound (69%).

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. temperatureto warm to r.t. where
  3. stirringstirring
  4. customwas judged complete by TLC (16 hr)
  5. extractionextracted with DCM (2×50 mL)
  6. dry with materialThe organics were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated to a solid
  9. customthat was recrystallized (EtOAc/Hex)

Sources & evidence

ORD record
ord-0d07b7590e494ced8a0450ef71f6a459
Source dataset
uspto-grants-2015_09
Patent number
US09133166B2

Reaction notes

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