Lithium Hydroxide → 6-Chloro-4-(2-fluoro-4-nitrobenzyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine

HRID 2240218Notes

Reaction equation

HRID 2240218 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=[CH:10][C:5]2=[C:4]([CH:19]([C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][C:25]=2[F:33])C(OC)=O)[CH:3]=1.[OH-].[Li+]>CO.O>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:17])([CH3:18])[CH3:16])[CH:9]=[CH:10][C:5]2=[C:4]([CH2:19][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][C:25]=2[F:33])[CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59304979HCID 59304979, compound

Product 1

HCID 593050056-Chloro-4-(2-fluoro-4-nitrobenzyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887MethanolSolvent

Procedure

358 mg (0.72 mmol) of methyl (6-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)(2-fluoro-4-nitrophenyl)acetate are dissolved in 6 ml of methanol. 21 mg (0.87 mmol) of lithium hydroxide and 2 drops of water are added, and the mixture is stirred at RT for 20 hours. The mixture is concentrated under reduced pressure, dichloromethane and water are added and the organic phase is separated off and dried over sodium sulfate. The solvent is removed under reduced pressure and the product is purified by chromatography on silica gel (mobile phase: dichloromethane). This gives an oil.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure, dichloromethane and water
  2. additionare added
  3. customthe organic phase is separated off
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe product is purified by chromatography on silica gel (mobile phase: dichloromethane)
  7. customThis gives an oil

Sources & evidence

ORD record
ord-18c7ba106e9b450d92f075b282fc6ae6
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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