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

HRID 986977Notes

Reaction equation

HRID 986977 reaction equation
[O-]CC.[Na+].[F:5][C:6]1[CH:26]=[CH:25][C:9]([C:10]([C:12]2[C:17]([O:18][CH2:19][C:20]([O:22]CC)=[O:21])=[CH:16][CH:15]=[CH:14][N:13]=2)=O)=[CH:8][CH:7]=1>C1(C)C=CC=CC=1>[C:20]([C:19]1[O:18][C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[C:10]=1[C:9]1[CH:25]=[CH:26][C:6]([F:5])=[CH:7][CH:8]=1)([OH:22])=[O:21]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 10881213Ethyl 2-[2-(4-fluorobenzoyl)pyridin-3-yloxy]acetate

Product 1

HCID 110650642-Carboxy-3-(4-fluorophenyl)-furo[3,2-b]pyridineYield 60.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Sodium ethoxide (1.51 g. 22.6 mmol) was suspended in toluene (25 ml) and ethyl 2-[2-(4-fluorobenzoyl)pyridin-3-yloxy]acetate (3.5 g, 11.5 mmol) was added. The reaction was heated at reflux under an argon atmosphere. After 12 h, the reaction mixture was cooled to room temperature and the product was extracted into water. The aqueous layer was acidified with hydrochloric acid to give 2-carboxy-3-(4-fluorophenyl)-furo[3,2-b]pyridine as a solid (1.8 g).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux under an argon atmosphere
  3. extractionthe product was extracted into water

Sources & evidence

ORD record
ord-f6a8a60873a748c0905b1373ceb9ef1b
Source dataset
uspto-grants-2003_10
Patent number
US06630485B2

Reaction notes

Loading…