N-(2-Fluoro-4-nitrophenyl)-3-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-4-amine → 2-Fluoro-N1-(3-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)benzene-1,4-diamine

HRID 2240229Notes

Reaction equation

HRID 2240229 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[NH:11][C:12]1[C:13]2[C:20]([CH3:21])=[CH:19][N:18]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:14]=2[N:15]=[CH:16][CH:17]=1>C(O)C.C1COCC1.[Pt-]=O>[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[NH:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]2[N:18]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:27])([CH3:29])[CH3:28])[CH:19]=[C:20]([CH3:21])[C:13]=12

Participants

4

Reactant 1

HCID 59304977N-(2-Fluoro-4-nitrophenyl)-3-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-4-amine

Product 1

HCID 593050122-Fluoro-N1-(3-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)benzene-1,4-diamine

Reagents, catalysts & solvents 2

HCID 178527100HCID 178527100, compoundCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

20 mg (50 μmol) of N-(2-fluoro-4-nitrophenyl)-3-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-4-amine are dissolved in 8 ml of a mixture of ethanol/THF (1:1). 11 mg (50 μmol) of platinum(I) oxide are added, and the mixture is stirred under a hydrogen atmosphere at atmospheric pressure overnight. The suspension is then filtered through Celite, the Celite is washed with a little ethanol and the solvent is removed under reduced pressure.

Workup

  1. filtrationThe suspension is then filtered through Celite
  2. washthe Celite is washed with a little ethanol
  3. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-0d40a151a60b4884b3f7e1914e8a3b3d
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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