Lithium Hydroxide → N-(2-Fluoro-4-nitrophenyl)-N-methyl-1H-pyrrolo[2,3-b]pyridine-4-amine

HRID 2240239Notes

Reaction equation

HRID 2240239 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]([CH3:29])[C:12]1[C:13]2[CH:20]=[CH:19][N:18](COCC[Si](C)(C)C)[C:14]=2[N:15]=[CH:16][CH:17]=1.FC(F)(F)C(O)=O.[OH-].[Li+].C(=O)(O)[O-].[Na+]>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]([CH3:29])[C:12]1[C:13]2[CH:20]=[CH:19][NH:18][C:14]=2[N:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 59304997N-(2-Fluoro-4-nitrophenyl)-N-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-4-amine

Product 1

HCID 59305010N-(2-Fluoro-4-nitrophenyl)-N-methyl-1H-pyrrolo[2,3-b]pyridine-4-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 71 mg (0.17 mmol) of N-(2-fluoro-4-nitrophenyl)-N-methyl-1-{[2-(trimethylsilyl)-ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-4-amine in 2 ml of dichloromethane and 1.0 ml (13.0 mmol) of trifluoroacetic acid is stirred at RT for 3 h. The reaction mixture is concentrated under reduced pressure, the residue is taken up in 2 ml of THF, 1.02 ml (1.02 mmol) of aqueous 1 M lithium hydroxide solution are added and the mixture is stirred at RT overnight. To bring the reaction to completion, a further 0.5 ml (0.5 mmol) of lithium hydroxide solution is added, and the mixture is stirred for another night. Saturated sodium bicarbonate solution is added to the mixture, and the mixture is extracted twice with ethyl acetate. 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. concentrationThe reaction mixture is concentrated under reduced pressure
  2. addition1.02 ml (1.02 mmol) of aqueous 1 M lithium hydroxide solution are added
  3. customthe reaction to completion
  4. stirringthe mixture is stirred for another night
  5. extractionthe mixture is extracted twice with ethyl acetate
  6. dry with materialThe combined organic phases are dried over magnesium sulfate
  7. customthe solvent is removed under reduced pressure
  8. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-3980c91f9e4a4236b676c3f04a6e17cb
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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