Trifluoroacetic acid → 5-Amino-2-fluoroisonicotinic acid

HRID 50822

Reaction equation

C(OC([NH:8][C:9]1[C:10]([C:16]([OH:18])=[O:17])=[CH:11][C:12]([F:15])=[N:13][CH:14]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>>[NH2:8][C:9]1[C:10]([C:16]([OH:18])=[O:17])=[CH:11][C:12]([F:15])=[N:13][CH:14]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 106110655-((tert-Butoxycarbonyl)amino)-2-fluoroisonicotinic acid

Product 1

HCID 27625115-Amino-2-fluoroisonicotinic acidYield 75.6%

Procedure

Reaction of 5-[N-(tert-butoxycarbonyl)amino]-2-fluoropyridine-4-carboxylic acid (1.0 g, 3.9 mmol) with TFA as described above gives 5-amino-2-fluoropyridine-4-carboxylic acid(0.46 g, 74). 1H NMR (DMSO) δ 7.85 (1H, d, J=1.5 Hz), 7.23 (1H, d, J 2.5 Hz).

Sources & evidence

ORD record: ord-5fadefd3dcde4b31a3bea03fd87765bc
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713484B2

Linked notes

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