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

HRID 408443Notes

Reaction equation

HRID 408443 reaction equation
Cl[Sn]Cl.[F:4][C:5]1[C:10]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[CH:9][N:8]=[C:7]2[NH:16][CH:17]=[C:18]([N+:19]([O-])=O)[C:6]=12.[OH-].[Na+]>Cl>[F:4][C:5]1[C:10]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[CH:9][N:8]=[C:7]2[NH:16][CH:17]=[C:18]([NH2:19])[C:6]=12

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 602057184-fluoro-5-(2-methoxyethoxy)-3-nitro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 602057194-fluoro-5-(2-methoxyethoxy)-1H-pyrrolo[2,3-b]pyridin-3-amineYield 95%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
2.5 °C

Procedure

SnCl2 (1337 mg, 7.05 mmol) was added to 4-fluoro-5-(2-methoxyethoxy)-3-nitro-1H-pyrrolo[2,3-b]pyridine (360 mg, 1.41 mmol) in 6N HCl (10 mL) at 0-5° C., and the reaction was stirred at 0-5° C. for 1 hour. 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 4-fluoro-5-(2-methoxyethoxy)-1H-pyrrolo[2,3-b]pyridin-3-amine (300 mg, 95% yield) as an oil.

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-5da4d0759c744fdcbc8685f753eca341
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

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