Methyl morpholine oxide → HCID 86686481, compound

HRID 1466786Notes

Reaction equation

HRID 1466786 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[C:10]([S:18][C:19]2[CH:20]=[C:21]([CH2:25][OH:26])[CH:22]=[CH:23][CH:24]=2)=[C:9]1[CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1>C(Cl)Cl.C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[C:10]([S:18][C:19]2[CH:20]=[C:21]([CH:22]=[CH:23][CH:24]=2)[CH:25]=[O:26])=[C:9]1[CH3:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 66765279HCID 66765279, compound

Product 1

HCID 86686481HCID 86686481, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

[3-(1-Benzyl-6-chloro-2-methyl-1H-indol-3-ylsulfanyl)-phenyl]-methanol (0.750 g, 1.9 mmol) was dissolved in DCM:ACN (9:1, 20 mL) then 4-methylmorpholine N-oxide (0.334 g, 2.85 mmol) and tetrapropylammonium perruthenate (0.067 g, 0.19 mmol) were added. After 30 minutes the reaction mixture was concentrated and loaded directly onto a silica gel column. Silica gel chromatography (0-30% EtOAc in hexanes) provided the title compound.

Workup

  1. concentrationAfter 30 minutes the reaction mixture was concentrated

Sources & evidence

ORD record
ord-0681a73aac3e4656800c63c2208fb774
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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