Sodium hydride → 2-[1,4]Diazepan-1-YL-1-(4-fluoro-benzyl)-1H-benzoimidazole

HRID 637225Notes

Reaction equation

HRID 637225 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[NH:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[H-].[Na+].[F:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=1>CN(C)C=O>[F:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][N:19]2[C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[N:16]=[C:15]2[N:11]2[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 184646551-t-butoxycarbonyl-4-(1H-benzimidazol-2-yl)[1,4]diazepane

Product 1

HCID 184649032-[1,4]Diazepan-1-YL-1-(4-fluoro-benzyl)-1H-benzoimidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Combine 1-(t-butoxycarbonyl)-4-(1H-benzimidazol-2-yl)[1,4]diazepane (1.5 g, 5.03 mmol) and dimethylformamide (30 mL). Add sodium hydride (0.27 g, 60%n in oil, 6.5 mmol). After 30 minutes, add 4-fluorobenzyl bromide (1.0 mL, 8.03 mmol). Heat to 80° C. After 2 hours, cool to ambient temperature and partition the reaction mixture between dichloromethane and a saturated aqueous sodium bicarbonate solutions. Separate the layers and extract the organic layer with brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give 1-(t-butoxycarbonyl)-4-(1-(4-fluorobenzyl-1H-benzimidazol-2-yl)[1,4]diazepane.

Workup

  1. waitAfter 2 hours
  2. temperaturecool to ambient temperature
  3. custompartition the reaction mixture between dichloromethane
  4. customSeparate the layers
  5. extractionextract the organic layer with brine
  6. dry with materialDry the organic layer over MgSO4
  7. filtrationfilter
  8. customevaporate in vacuo

Sources & evidence

ORD record
ord-2d6fa46911a340f586dd58d0d737c3e9
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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