Carbon Dioxide → 2-Fluoro-6-phenylpyridine-3-carboxylic acid

HRID 2053696Notes

Reaction equation

HRID 2053696 reaction equation
[Li+].CC([N-]C(C)C)C.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:11]=1.[C:22](=[O:24])=[O:23].Cl>C1COCC1>[F:9][C:10]1[C:15]([C:22]([OH:24])=[O:23])=[CH:14][CH:13]=[C:12]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:11]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 2724682Lithium diisopropylamide2×HCID 27628912-fluoro-6-phenylpyridine

Product 1

HCID 463149432-Fluoro-6-phenylpyridine-3-carboxylic acidYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Cool a solution of LDA (3.46 mmol) in anhydrous THF (6 mL) to −78° C. Cannulate the 2-fluoro-6-phenylpyridine in anhydrous THF (6 mL) to the cooled LDA solution. Stir at −78 (C for 30 minutes then bubble carbon dioxide gas through the solution for 10 minutes. Allow the reaction to come to room temperature and purge with argon. Extract the reaction with 1 M NaOH and discard the organics. Acidify the aqueous layer with conc. HCl and extract with ethyl acetate. Dry the organic layer over MgSO4, filter and evaporate to yield the title compound as a light yellow solid (405 mg, 65%). MS (m/e): 216.1 (M−).

Workup

  1. customAllow the reaction
  2. customto come to room temperature
  3. custompurge with argon
  4. extractionExtract
  5. customthe reaction with 1 M NaOH
  6. extractionextract with ethyl acetate
  7. dry with materialDry the organic layer over MgSO4
  8. filtrationfilter
  9. customevaporate

Sources & evidence

ORD record
ord-b6d0db8cbb6548eb98cf590bd10ec4a2
Source dataset
uspto-grants-2008_02
Patent number
US07326731B2

Reaction notes

Loading…