Nitric Acid → 5-bromo-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridine

HRID 408164Notes

Reaction equation

HRID 408164 reaction equation
[Br:1][C:2]1[C:3]([F:11])=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[N+:12]([O-])([OH:14])=[O:13]>>[Br:1][C:2]1[C:3]([F:11])=[C:4]2[C:10]([N+:12]([O-:14])=[O:13])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 534129385-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 602052755-bromo-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridineYield 76%

Conditions

Temperature
0 °C

Procedure

5-Bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridine (10 g, 47 mmol) was added to fuming nitric acid (50 mL) at 0° C., and the reaction was stirred at 0° C. for 30 minutes. Ice (300 mL) was added, and the reaction was allowed to warm to room temperature. The resulting suspension was filtered and dried under high vacuum to provide 5-bromo-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridine (9.2 g, 76% yield) as a solid. 1H NMR (400 MHz, (CD3)2SO) δ 13.63 (br s, 1H), 8.85 (s, 1H), 8.56 (d, 1H).

Workup

  1. temperatureto warm to room temperature
  2. filtrationThe resulting suspension was filtered
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-5c0a3d73421345e98f204d64eab27870
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

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