Water → N-(2-Fluoro-4-nitrophenyl)-N-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-4-amine

HRID 2240238Notes

Reaction equation

HRID 2240238 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:11][C:12]1[C:13]2[CH:20]=[CH:19][N:18]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:14]=2[N:15]=[CH:16][CH:17]=1.[H-].[Na+].[CH3:31]I.O>CC(N(C)C)=O>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]([CH3:31])[C:12]1[C:13]2[CH:20]=[CH:19][N:18]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:14]=2[N:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11647045N-(2-Fluoro-4-nitrophenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-4-amine

Product 1

HCID 59304997N-(2-Fluoro-4-nitrophenyl)-N-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-4-amine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

A solution of 100 mg (0.25 mmol) of N-(2-fluoro-4-nitrophenyl)-1-{[2-(trimethyl-silyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-4-amine in 0.75 ml of DMA is added dropwise to a suspension of 30 mg (0.75 mmol) of sodium hydride in 0.75 ml of DMA, and the mixture is stirred at RT for 30 min. 77 μl (1.24 mmol) of methyl iodide are then slowly added dropwise, and the mixture is stirred for a further 30 min. Water is then added, and the mixture is extracted twice with dichloromethane. The combined organic phases are dried over magnesium sulfate, the solvent is removed under reduced pressure and the residue is purified by preparative HPLC.

Workup

  1. stirringthe mixture is stirred for a further 30 min
  2. extractionthe mixture is extracted twice with dichloromethane
  3. dry with materialThe combined organic phases are dried over magnesium sulfate
  4. customthe solvent is removed under reduced pressure
  5. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-2e9ff9025a834f9282b9f62f06814298
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

Loading…