Selenium Dioxide → HCID 59594306, compound

HRID 1623072Notes

Reaction equation

HRID 1623072 reaction equation
[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@:3]21[CH2:24][C:13]1[CH:14]=[C:15]3[C:20](=[CH:21][C:12]=1[CH2:11]2)[N:19]=[C:18]([CH:22]=[O:23])[CH:17]=[CH:16]3.[Se](=O)=[O:26]>O1CCOCC1.O>[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@:3]21[CH2:24][C:13]1[CH:14]=[C:15]3[C:20](=[CH:21][C:12]=1[CH2:11]2)[N:19]=[C:18]([C:22]([OH:26])=[O:23])[CH:17]=[CH:16]3

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 59594285(S)-2'-Oxo-1',2',6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridine]-2-carbaldehyde2×

Product 1

HCID 59594306HCID 59594306, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of (S)-2-methyl-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (500 mg, 1.66 mmol, described in Intermediate 6) and selenium dioxide (552 mg, 4.97 mmol) in dioxane (30 mL) and H2O (3 mL) was heated at reflux for 18 h. The reaction mixture was allowed to cool, then it was filtered through a pad of Celite, and the filtrate was concentrated in vacuo to give the title compound. MS: m/z=332 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. temperatureto cool
  4. filtrationit was filtered through a pad of Celite
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-cf2407fb3ef647fb835a3c9960a9fad0
Source dataset
uspto-grants-2014_07
Patent number
US08778957B2

Reaction notes

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