Benzyl Bromide → HCID 11533506, compound

HRID 730796Notes

Reaction equation

HRID 730796 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:27]=[CH:26][C:6]2[N:7]=[C:8]([N:10]3[CH2:15][CH2:14][N:13]([C:16]4[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:19]=[CH:18][N:17]=4)[CH2:12][CH2:11]3)[NH:9][C:5]=2[CH:4]=1.[H-].[Na+].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C=O)C>[CH2:32]([N:7]1[C:6]2[CH:26]=[CH:27][C:3]([C:2]([F:1])([F:28])[F:29])=[CH:4][C:5]=2[N:9]=[C:8]1[N:10]1[CH2:15][CH2:14][N:13]([C:16]2[C:21]([C:22]([F:23])([F:24])[F:25])=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:12][CH2:11]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 11647318HCID 11647318, compound

Product 1

HCID 11533506HCID 11533506, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(trifluoromethyl)-2-{4-[3-(trifluoromethyl)(2-pyridyl)]piperazinyl}benzoimidazole (415 mg, 1.0 mmol, Example 53) in anhydrous DMF (5 mL, Aldrich) was added sodium hydride (72 mg, 50% in mineral oil, 1.5 mmol, Aldrich) at 0° C. The reaction mixture was stirred at room temperature for 0.5 h. After the mixture was cooled to 0° C., it was treated with benzyl bromide (171 mg, 1.0 mmol, Aldrich) and stirred at room temperature for 16 h. The reaction was then quenched with saturated aqueous solution of NaHCO3 (30 mL) and extracted with EtOAc (2×50 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (25% EtOAc/hexane) to give the title compound as white solid. MS (ESI, pos. ion) m/z: 506.2 (M+1).

Workup

  1. temperatureAfter the mixture was cooled to 0° C.
  2. stirringstirred at room temperature for 16 h
  3. customThe reaction was then quenched with saturated aqueous solution of NaHCO3 (30 mL)
  4. extractionextracted with EtOAc (2×50 mL)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (25% EtOAc/hexane)

Sources & evidence

ORD record
ord-9db020fb89e04b2a8dc450a9c6ef4043
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Reaction notes

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