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

HRID 79612Notes

Reaction equation

HRID 79612 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]>O>[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

4

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 86.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridine (0.100 g, 0.465 mmol, see Example 51) was added slowly to fuming HNO3 (5 mL) at 0° C. and stirred for 10 minutes. Ice was then added, followed by the addition of water. The resulting solid product was then filtered, and washed with water and dried to give 5-bromo-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridine (0.105 g, 86.8% yield).

Workup

  1. additionIce was then added
  2. filtrationThe resulting solid product was then filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-13fe756dd6144800b6353bd8783effc1
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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