Water → 4-Bromo-6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole

HRID 1024070Notes

Reaction equation

HRID 1024070 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[CH:5]=[C:4]([Cl:11])[CH:3]=1.[H-].[Na+].[CH3:14][Si:15]([CH3:22])([CH3:21])[CH2:16][CH2:17][O:18][CH2:19]Cl.O>CN(C)C=O>[Br:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:19][O:18][CH2:17][CH2:16][Si:15]([CH3:22])([CH3:21])[CH3:14])[C:6]=2[CH:5]=[C:4]([Cl:11])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 866841377-Bromo-5-chloro-1H-benzimidazole

Product 1

HCID 866841484-Bromo-6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazoleYield 77.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-6-chloro-1H-benzo[d]imidazole 109c (3.5 g, 15 mmol) in N,N-dimethylformamide (30 mL) was added sodium hydride (360 mg, 15 mmol) and 2-(trimethylsilyl)ethoxymethyl chloride (2.7 g, 16.5 mmol). The reaction was stirred at room temperature for 2 h. Water (100 mL) was added to quench the reaction. The mixture was extracted with ethyl acetate (3×80 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure to afford 116a as a brown solid (4.2 g, 77%). MS-ESI: [M+H]+ 361.0

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted with ethyl acetate (3×80 mL)
  4. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a54b33a70e0241f19cd444b614f039b1
Source dataset
uspto-grants-2014_05
Patent number
US08722676B2

Reaction notes

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