2-Carboxy-3-(4-fluorophenyl)-furo[3,2-b]pyridine → 3-(4-Fluorophenyl)-furo[3,2-b]pyridine

HRID 429205Notes

Reaction equation

HRID 429205 reaction equation
C([C:4]1[O:12][C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)(O)=O>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[F:19][C:16]1[CH:15]=[CH:14][C:13]([C:5]2[C:6]3=[N:7][CH:8]=[CH:9][CH:10]=[C:11]3[O:12][CH:4]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 1

HCID 110650642-Carboxy-3-(4-fluorophenyl)-furo[3,2-b]pyridine

Product 1

HCID 229879853-(4-Fluorophenyl)-furo[3,2-b]pyridineYield 57%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Procedure

A mixture of 2-carboxy-3-(4-fluorophenyl)-furo[3,2-b]pyridine (1.8 g, 7 mmol), copper metal (0.56 g, 8.81 mmol) in quinoline (10 ml) was heated at reflux. After 45 min., the reaction was cooled to room temperature and the product was extracted into water. The aqueous layer was acidified with hydrochloric acid and acetic acid. The product was filtered and dissolved in ether. The ether layer was dried over sodium sulfate and concentrated in vacua. Purification by flash chromatography using ethyl acetate-hexanes (1:9) as the eluant gave 3-(4-fluorophenyl)-furo[3,2-b]pyridine as a solid (0.85 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. extractionthe product was extracted into water
  4. filtrationThe product was filtered
  5. dissolutiondissolved in ether
  6. dry with materialThe ether layer was dried over sodium sulfate
  7. concentrationconcentrated in vacua
  8. customPurification by flash chromatography

Sources & evidence

ORD record
ord-d8b88c8b0ffc4fe2979cce21aecaf622
Source dataset
uspto-grants-2001_11
Patent number
US06316464B1

Reaction notes

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