Sodium hydride → HCID 86729285, compound

HRID 1399889Notes

Reaction equation

HRID 1399889 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:13][Si:14]([CH2:17][CH2:18][O:19][CH2:20]Cl)([CH3:16])[CH3:15]>C1COCC1>[Br:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:20][O:19][CH2:18][CH2:17][Si:14]([CH3:16])([CH3:15])[CH3:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 112525844-Bromo-1H-benzimidazole

Product 1

HCID 86729285HCID 86729285, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-bromo-1H-benzo[d]imidazole (1.1 g, 5.6 mmol) in THF was added NaH (448 mg, 11.2 mmol) at 0° C. After stirring at for 30 minutes at room temperature 0° C., SEM-Cl (1.4 g, 8.4 mmol) was added to the mixture at 0° C. The mixture was then stirred at room temperature for 16 h, at which time TLC showed the completion of the reaction. The reaction was quenched by addition of aq. NH4Cl and the mixture extracted with ethyl acetate with the combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuum to give the desired product and used in the next step without further purification (1.65 g, Yield 90%). LCMS (m/z): 229.0 (M+1)

Workup

  1. stirringThe mixture was then stirred at room temperature for 16 h, at which time TLC
  2. customthe completion of the reaction
  3. customThe reaction was quenched by addition of aq. NH4Cl
  4. extractionthe mixture extracted with ethyl acetate with the combined organic layers
  5. dry with materialwere dried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-eaa7fc6237234e7ca808f07c5c4e1d34
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

Loading…