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

HRID 986978Notes

Reaction equation

HRID 986978 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 vacuo. 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 vacuo
  8. customPurification by flash chromatography

Sources & evidence

ORD record
ord-269a711765124372b4a752e8ec7046a9
Source dataset
uspto-grants-2003_10
Patent number
US06630485B2

Reaction notes

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