Sodium Chloride → 6-Bromo-7-chloro-3-[[2-(trimethylsilyl)ethoxy]methyl]-3H-imidazo[4,5-b]pyridine

HRID 1506225Notes

Reaction equation

HRID 1506225 reaction equation
[Br:1][C:2]1[C:3]([Cl:11])=[C:4]2[N:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].Cl[CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20].[Cl-].[Na+]>CN(C)C=O>[Br:1][C:2]1[C:3]([Cl:11])=[C:4]2[N:10]=[CH:9][N:8]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178477812HCID 178477812, compound

Product 1

HCID 712584796-Bromo-7-chloro-3-[[2-(trimethylsilyl)ethoxy]methyl]-3H-imidazo[4,5-b]pyridineYield 38.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Bromo-7-chloro-3H-imidazo[4,5-b]pyridine (1.07 g, 4.60 mmol) in N,N-dimethylformamide (12 mL) was cooled to 0° C., mixed with sodium hydride (55 wt % dispersion in mineral oil, 300 mg, 6.88 mmol) and [2-(chloromethoxy)ethyl]trimethylsilane (12.0 mL, 6.78 mmol) and stirred at room temperature for 3 hours. After addition of saturated aqueous sodium chloride, the reaction mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1→5/1 (v/v)) to give the title compound as a yellow oil (640 mg, yield 38%).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1→5/1 (v/v))

Sources & evidence

ORD record
ord-e2dfd12a794f4408aac2982972156397
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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