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

HRID 408442Notes

Reaction equation

HRID 408442 reaction equation
[F:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][O:11][CH3:12])=[CH:6][N:5]=[C:4]2[NH:13][CH:14]=[CH:15][C:3]=12.[N+:16]([O-])([OH:18])=[O:17]>>[F:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][O:11][CH3:12])=[CH:6][N:5]=[C:4]2[NH:13][CH:14]=[C:15]([N+:16]([O-:18])=[O:17])[C:3]=12

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 60205717HCID 60205717, compound

Product 1

HCID 602057184-fluoro-5-(2-methoxyethoxy)-3-nitro-1H-pyrrolo[2,3-b]pyridineYield 67%

Procedure

4-Fluoro-5-(2-methoxyethoxy)-1H-pyrrolo[2,3-b]pyridine (440 mg, 2.09 mmol) was added to HNO3 fuming (4 mL) at 0-5° C., and the reaction was stirred for 15 minutes. Ice was added, and the resulting solid was filtered and dried to yield 4-fluoro-5-(2-methoxyethoxy)-3-nitro-1H-pyrrolo[2,3-b]pyridine (360 mg, 67% yield) as a solid.

Workup

  1. additionIce was added
  2. filtrationthe resulting solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-072ecd3362e1408ebc8e15c8624b082f
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

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