Sodium hydride → HCID 89971437, compound

HRID 1027249Notes

Reaction equation

HRID 1027249 reaction equation
[Br:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:5]2[NH:6][C:7]([CH3:9])=[N:8][C:4]=2[CH:3]=1.[H-].[Na+].[CH3:16][Si:17]([CH3:24])([CH3:23])[CH2:18][CH2:19][O:20][CH2:21]Cl.C(Cl)Cl.CO>CN(C=O)C>[Br:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:5]2[N:6]([CH2:21][O:20][CH2:19][CH2:18][Si:17]([CH3:24])([CH3:23])[CH3:16])[C:7]([CH3:9])=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 21226129Dichloromethane methanolHCID 178486899HCID 178486899, compound

Product 1

HCID 89971437HCID 89971437, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-bromo-6-methoxy-2-methyl-1H-benzo[d]imidazole (400 mg, 1.659 mmol) in DMF (3 mL) was added 60% wt NaH (80 mg, 1.991 mmol) at 0° C. The mixture was stirred from 0° C. to room temperature for 0.5 hours, then 2-trimethylsilylethyoxymethyl chloride (SEMCl, 0.352 mL, 1.991 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 2 hours then quenched with water and extracted with DCM. The organic phase was dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (10-100% EtOAc/Heptane then 0-10% DCM/MeOH) to afford the title compound (310 mg, 50.3% yield) as an oil. MS (M+1)=373.1.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 hours
  2. customthen quenched with water
  3. extractionextracted with DCM
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (10-100% EtOAc/Heptane

Sources & evidence

ORD record
ord-80837b351324425abb50693d6e647fd7
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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