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

Reaction equation

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

Participants

Reactant 2

HCID 944Nitric Acid

HCID 60205637HCID 60205637, compound

Product 1

HCID 602056385-ethoxy-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridineYield 78%

Conditions

Temperature: 0 °C

Procedure

Cold (about 0 to about 5° C.) fuming nitric acid (10 mL) was added to 5-ethoxy-4-fluoro-1H-pyrrolo[2,3-b]pyridine (340 mg, 0.944 mmol). The reaction was stirred at 0° C. for 15 minutes and then ice was added. The resulting solid was filtered and dried to yield 5-ethoxy-4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridine (165 mg, 78% yield) as a solid.

Workup

additionice was added
filtrationThe resulting solid was filtered
customdried

Sources & evidence

ORD record: ord-f28dc064195844e091f4e6007fc88506
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08545897B2

Reaction notes

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