Isopropanol → 5-chloro-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

HRID 1923944Notes

Reaction equation

HRID 1923944 reaction equation
[Cl:1][C:2]1[C:3]([F:14])=[C:4]2[C:10]([N+:11]([O-])=O)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.CC(O)C>C1COCC1.[Pt]>[Cl:1][C:2]1[C:3]([F:14])=[C:4]2[C:10]([NH2:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 3776IsopropanolHCID 602052745-chloro-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 581955655-chloro-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amineYield 108.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5-Chloro-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridine (1.00 g, 4.6 mmol) and platinum-0.5% Fe (0.452 g, 0.06 mmol) were suspended in THF (12.4 mL) with IPA (6.2 mL). The mixture was hydrogenated at 20 psi for 20 hours, and then the catalyst was removed by filtration. The filtrate was concentrated to dryness, and 5-chloro-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (923 mg, 107% yield) was isolated as a solid.

Workup

  1. customthe catalyst was removed by filtration
  2. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-43da28942eed45ff8ba82d8d7aa66110
Source dataset
uspto-grants-2012_05
Patent number
US08178131B2

Reaction notes

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