Carbon Dioxide → 5-((tert-Butoxycarbonyl)amino)-2-fluoroisonicotinic acid

HRID 1386196Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([F:15])=[N:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.[C:21](=[O:23])=[O:22]>>[C:1]([O:5][C:6]([NH:8][C:9]1[C:10]([C:21]([OH:23])=[O:22])=[CH:11][C:12]([F:15])=[N:13][CH:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 3

HCID 280Carbon Dioxide

HCID 11031143tert-Butyl (6-fluoropyridin-3-yl)carbamate

HCID 178418339Butyllithium

Product 1

HCID 106110655-((tert-Butoxycarbonyl)amino)-2-fluoroisonicotinic acidYield 25%

Procedure

Reaction of 5-[N-(tert-butoxycarbonyl)amino]-2-fluoropyridine (5.3 g, 25 mmol) sequentially with n-BuLi and CO2 as described in the following example gives 5-[N-(tert-butoxycarbonyl)amino]-2-fluoropyridine-4-carboxylic acid (1.60 g, 25%). 1H NMR (DMSO) δ 9.83 (1H, brs), 8.84 (1H, s), 7.49 (1H, d, J=2.9 Hz), 1.47 (9H, s).

Sources & evidence

ORD record: ord-4386b5a174504d5f8c185bb2cd4b0a38
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265410B1

Reaction notes

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