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

HRID 637226Notes

Reaction equation

HRID 637226 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

Procedure

Alternately, combine 1-(t-butoxycarbonyl)-4-(1H-benzimidazol-2-yl)[1,4]diazepane (1.7 g, 5.37 mmol) and dimethylformamide (40 mL). Add sodium hydride (0.23 g, 60% n in oil, 5.75 mmol). After 15 minutes, add 4-fluorobenzyl bromide (0.73 mL, 5.86 mmol). After 18 hours, partition the reaction mixture between dichloromethane and a saturated aqueous sodium bicarbonate solution. Separate the layers and extract the organic layer five times with water and then brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give 1-(t-butoxycarbonyl)-4-(1-(4-fluorobenzyl-1H-benzimidazol-2-yl)[1,4]diazepane: Rf=0.42 (silica gel, 50% ethyl acetate/hexane).

Workup

  1. waitAfter 18 hours
  2. custompartition the reaction mixture between dichloromethane
  3. customSeparate the layers
  4. extractionextract the organic layer five times with water
  5. dry with materialDry the organic layer over Na2SO4
  6. filtrationfilter
  7. customevaporate in vacuo

Sources & evidence

ORD record
ord-f11a8d8ec2594f3b9b671c91f922686f
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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