Sodium Hydroxide → 5-ethoxy-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

HRID 408394Notes

Reaction equation

HRID 408394 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[CH2:6]([O:8][C:9]1[C:10]([F:21])=[C:11]2[C:17]([N+:18]([O-])=O)=[CH:16][NH:15][C:12]2=[N:13][CH:14]=1)[CH3:7].[OH-].[Na+]>Cl>[CH2:6]([O:8][C:9]1[C:10]([F:21])=[C:11]2[C:17]([NH2:18])=[CH:16][NH:15][C:12]2=[N:13][CH:14]=1)[CH3:7]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24287Tin tetrachlorideHCID 602056385-ethoxy-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 602056395-ethoxy-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amineYield 86.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Tin chloride (674 mg, 3.55 mmol) was added to 5-ethoxy-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridine (160 mg, 0.711 mmol) in 6N HCl (5 mL) at about 0 to about 5° C., and then the reaction was stirred at 0 to about 5° C. for 2 hours. The solution was neutralized by addition of 6N NaOH and then extracted with CHCl3/IPA (3:1). The combined organic phases were dried over MgSO4 and concentrated to leave 5-ethoxy-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (120 mg, 86% yield) as a solid.

Workup

  1. extractionextracted with CHCl3/IPA (3:1)
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-42b3c9b93ce24fa08ec0dddbaaefd14e
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

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