Sodium hydride → 6-Chloro-4-nitro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine

HRID 2240210Notes

Reaction equation

HRID 2240210 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:9]=[C:8]2[NH:10][CH:11]=[CH:12][C:7]2=[C:6]([N+:13]([O-:15])=[O:14])[CH:5]=1.[CH3:16][Si:17]([CH3:24])([CH3:23])[CH2:18][CH2:19][O:20][CH2:21]Cl>CN(C)C=O>[Cl:3][C:4]1[N:9]=[C:8]2[N:10]([CH2:21][O:20][CH2:19][CH2:18][Si:17]([CH3:24])([CH3:23])[CH3:16])[CH:11]=[CH:12][C:7]2=[C:6]([N+:13]([O-:15])=[O:14])[CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 179793386-chloro-4-nitro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 469416086-Chloro-4-nitro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At 0° C. and under an atmosphere of argon, 1.34 g (28.3 mmol) of sodium hydride (60% in mineral oil) are added in small portions to a solution of 5.6 g (28.3 mmol) of 6-chloro-4-nitro-1H-pyrrolo[2,3-b]pyridine in dimethylformamide (50 ml), and the suspension is stirred at RT for 30 minutes. The mixture is once more cooled to 0° C., 5.3 ml (29.8 mmol of 2-(trimethylsilyl)ethoxymethyl chloride are added dropwise and the mixture is allowed to stir at room temperature for 2 h. The suspension is poured into ice-water (250 ml) and stirred until the mixture has reached RT. The mixture is then extracted with ethyl acetate (three times 50 ml) and the organic phase is washed with saturated sodium chloride solution. The solution is dried over magnesium sulfate and concentrated. The residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 6:1).

Workup

  1. temperatureThe mixture is once more cooled to 0° C.
  2. stirringto stir at room temperature for 2 h
  3. stirringstirred until the mixture
  4. customhas reached RT
  5. extractionThe mixture is then extracted with ethyl acetate (three times 50 ml)
  6. washthe organic phase is washed with saturated sodium chloride solution
  7. dry with materialThe solution is dried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 6:1)

Sources & evidence

ORD record
ord-56935cc8ee1649588cf966d732b15bb7
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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