HCID 72532772, compound → HCID 59214363, compound

HRID 552816Notes

Reaction equation

HRID 552816 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([O:11][N:12]=[C:13]([C:15]2[C:16]3[CH:17]=[CH:18][NH:19][C:20]=3[CH:21]=[CH:22][CH:23]=2)[NH2:14])=O)[CH:5]=[N:6][C:7]=1[Cl:8]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[O:11][N:12]=[C:13]([C:15]3[CH:23]=[CH:22][CH:21]=[C:20]4[C:16]=3[CH:17]=[CH:18][NH:19]4)[N:14]=2)[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

3

Reactant 1

HCID 72532772HCID 72532772, compound

Product 1

HCID 59214363HCID 59214363, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N2-{[(5,6-Dichloropyridin-3-yl)carbonyl]oxy}-1H-indole-4-carboxamidine (1.91 g) was added to dioxane (40 ml), followed by heating under reflux for 5 hours. It was concentrated under reduced pressure, and then purified by silica gel column chromatography (EtOAc). To the obtained solid was added acetone, followed by suspension under heating. After being left to be cooled, the insolubles was collected by filtration to obtain 4-[5-(5,6-dichloropyridin-3-yl)-1,2,4-oxadiazol-3-yl]-1H-indole (1.44 g) as pale yellow powders.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 5 hours
  3. concentrationIt was concentrated under reduced pressure
  4. custompurified by silica gel column chromatography (EtOAc)
  5. additionTo the obtained solid was added acetone
  6. temperatureunder heating
  7. waitAfter being left
  8. temperatureto be cooled
  9. filtrationthe insolubles was collected by filtration

Sources & evidence

ORD record
ord-48519a9665e24e1aa056c882a4131953
Source dataset
uspto-grants-2011_05
Patent number
US07951825B2

Reaction notes

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