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

HRID 1034907Notes

Reaction equation

HRID 1034907 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-f607699eeb9d4b8da7850bd53ec6649c
Source dataset
uspto-grants-2013_10
Patent number
US08545897B2

Reaction notes

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