2-(4-Fluorophenyl)-2-(3-nitropyridin-2-yl)-1-(pyridin-4-yl)ethanone → 3-(4-Fluorophenyl)-1-Hydroxy-2-(Pyridin-4-Yl)-1h-Pyrrolo(3,2-B)Pyridine

HRID 659945Notes

Reaction equation

HRID 659945 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:17]2[C:22]([N+:23]([O-:25])=O)=[CH:21][CH:20]=[CH:19][N:18]=2)[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=O)=[CH:4][CH:3]=1>C(O)C.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:22]3[N:23]([OH:25])[C:9]=2[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 117274532-(4-Fluorophenyl)-2-(3-nitropyridin-2-yl)-1-(pyridin-4-yl)ethanone

Product 1

HCID 52882383-(4-Fluorophenyl)-1-Hydroxy-2-(Pyridin-4-Yl)-1h-Pyrrolo(3,2-B)PyridineYield 33.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

23 g (68.2 mmoles) of 2-(4-Fluoro-phenyl)-2-(3-nitro-pyridin-2-yl)-1-pyridin-4-yl-ethanone is dissolved in 700 mL of absolute ethanol. 2.2 g of 10% Palladium on charcoal is added to the solution which is stirred for 6 hours under a hydrogen atmosphere. The reaction mixture is filtered over celite, concentrated and the brown residue is purified by chromatography on silica gel (ethylacetate) to give 7 g of 3-(4-Fluoro-phenyl)-2-pyridin-4-yl-pyrrolo[3,2-b]pyridin-1-ol and 13 g of the starting material is recovered.

Workup

  1. filtrationThe reaction mixture is filtered over celite,
  2. concentrationconcentrated
  3. customthe brown residue is purified by chromatography on silica gel (ethylacetate)

Sources & evidence

ORD record
ord-7afc36fb9664423dbc0b08a375162ebc
Source dataset
uspto-grants-2011_12
Patent number
US08084395B2

Reaction notes

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