Sodium Hydroxide → 4-chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-amine

HRID 875666Notes

Reaction equation

HRID 875666 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]2[NH:12][CH:13]=[C:14]([N+:15]([O-])=O)[C:3]=12.[OH-].[Na+]>Cl>[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:9])[F:10])=[CH:6][N:5]=[C:4]2[NH:12][CH:13]=[C:14]([NH2:15])[C:3]=12

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 602053074-chloro-3-nitro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 602053084-chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-amineYield 90.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

SnCl2 dihydrate (0.85 g, 3.77 mmol) at a temperature of about 0° C. to about 5° C. was added to 4-chloro-3-nitro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine (0.20 g, 0.75 mmol) in 6M HCl (5 mL). The mixture was stirred at room temperature for 2 hours, and was then neutralized to a pH of about 8 with a 6N NaOH solution. The mixture was extracted with CHCl3:IPA (3×30 mL; 3:1) and dried over sodium sulfate. After removal of the solvent, 4-chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-amine (0.16 g, 89% yield) was isolated as a solid.

Workup

  1. extractionThe mixture was extracted with CHCl3
  2. dry with materialIPA (3×30 mL; 3:1) and dried over sodium sulfate
  3. customAfter removal of the solvent

Sources & evidence

ORD record
ord-e82a1c2449714d1f91b19a91df702ff5
Source dataset
uspto-grants-2015_03
Patent number
US08981085B2

Reaction notes

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