8-Bromo-2,3-dihydro-2-phenylbenzofuro[3,2-b]pyridin-4(1H)-one → HCID 178515547, compound

HRID 869381Notes

Reaction equation

HRID 869381 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][C:13]3[C:12](=[O:15])[CH2:11][CH:10]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[NH:9][C:8]=3[C:6]=2[CH:7]=1>O1CCOCC1>[OH:15][C:12]1[CH:11]=[C:10]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:9]=[C:8]2[C:6]3[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=3[O:14][C:13]=12

Participants

3

Reactant 1

HCID 867222268-Bromo-2,3-dihydro-2-phenylbenzofuro[3,2-b]pyridin-4(1H)-one

Product 1

HCID 178515547HCID 178515547, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 8-bromo-2-phenyl-2,3-dihydro-benzofuro[3,2-b]pyridin-4(1H)-one (23.8 g, 69.55 mmol) and FeCl3.6H2O (112.78 g, 417.3 mmol) was added to 1,4-dioxane (300 mL) The mixture was refluxed for 16 hours. TLC showed the reaction completed. The mixture was cooled to room temperature and poured into ice-water (500 mL) The yellow solids precipitated out were collected by filtration to give 4-hydroxyl-8-bromo-2-phenyl-benzofuro[3,2-b]pyridine (6D) (15.7 g, 66.36% yield).

Workup

  1. temperaturewas refluxed for 16 hours
  2. customprecipitated out
  3. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-be9f570e763e4c53827843eece0af0a4
Source dataset
uspto-grants-2015_03
Patent number
US08969373B2

Reaction notes

Loading…