HCID 58443296, compound → HCID 58443257, compound

HRID 1630754Notes

Reaction equation

HRID 1630754 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[N:13][C:12]([CH2:16][OH:17])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]>CC(C)=O.[O-2].[Mn+4].[O-2]>[CH2:1]([N:3]1[C:15]2[CH:14]=[N:13][C:12]([CH:16]=[O:17])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

Participants

4

Reactant 1

HCID 58443296HCID 58443296, compound

Product 1

HCID 58443257HCID 58443257, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 180AcetoneSolvent

Procedure

To a solution of (9-ethyl-9H-β-carbolin-3-yl)-methanol (560 mg, 2.47 mmol, 1 eq) in acetone (20 mL) was added manganese (IV) oxide (2.942 g, 33.84 mmol, 14 eq). The solution was stirred at rt. After 3 d, as only 50% conversion is observed, more manganese (IV) oxide was added (229 mg, 2.63 mmol, 1.1 eq) and the mixture was heated to 50° C. for 2.5 d. After this time, the reaction was cooled down to rt, filtered through CELITE®, and the solid was washed with dichloromethane. The filtrates were combined and concentrated under reduced pressure. The residue was purified by column chromatography eluting with ethyl acetate to give the title compound as a yellow oil. Mass Spec m/z=225 [M+H+].

Workup

  1. temperaturethe mixture was heated to 50° C. for 2.5 d
  2. temperatureAfter this time, the reaction was cooled down to rt
  3. filtrationfiltered through CELITE®
  4. washthe solid was washed with dichloromethane
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-198bf40d1c804e0eb1a5cc9b78c0f747
Source dataset
uspto-grants-2014_07
Patent number
US08791147B2

Reaction notes

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