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

HRID 2203992Notes

Reaction equation

HRID 2203992 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-87d3c71e26624fbf8b18bddd8443cd1e
Source dataset
uspto-grants-2016_06
Patent number
US09365568B2

Reaction notes

Loading…