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

HRID 1017670Notes

Reaction equation

HRID 1017670 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-27fdbad67cbd40e7b11382cb25586ec4
Source dataset
uspto-grants-2002_11
Patent number
US06479507B2

Reaction notes

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