Carbon Dioxide → 5-Fluoro-2-phenylisonicotinic acid

HRID 39515Notes

Reaction equation

HRID 39515 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][CH:7]=1.C([Li])CCC.[C:19](=[O:21])=[O:20].CO>O1CCCC1>[F:1][C:2]1[C:3]([C:19]([OH:21])=[O:20])=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 887MethanolHCID 463149355-Fluoro-2-phenylpyridineHCID 178418339Butyllithium

Product 1

HCID 463149505-Fluoro-2-phenylisonicotinic acidYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-45 °C

Procedure

To a solution of 5-fluoro-2-phenylpyridine (760.0 mg, 4.39 mmol) in tetrahydrofuran (15.0 ml) was added n-butyllithium (2.11 ml, 2.50 M in THF, 5.27 mmol) at −45° C. The mixture was stirred for 1 h at −45° C., then poured into THF containing dry ice. Stirred for 1 h, then MeOH (2 ml) was added. The solution was concentrated, and purified on Flashmaster II to get 560 mg (58%) of 5-fluoro-2-phenylisonicotinic acid.

Workup

  1. stirringStirred for 1 h
  2. concentrationThe solution was concentrated
  3. custompurified on Flashmaster II

Sources & evidence

ORD record
ord-6fead46572f64c71852aa859ca9dea62
Source dataset
uspto-grants-2013_09
Patent number
US08524911B2

Reaction notes

Loading…