Hexane → 2-(5-Nitro-indol-1-yl)-3-phenyl-propionic acid methyl ester

HRID 2245510Notes

Reaction equation

HRID 2245510 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:19][O:20][C:21](=[O:38])[CH:22](OS(C(F)(F)F)(=O)=O)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CCCCCC>CC(C)=O.CCOC(C)=O>[CH3:19][O:20][C:21](=[O:38])[CH:22]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH:7]=[CH:8]1)[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 10796Cesium carbonateHCID 225235-NitroindoleHCID 13388932alpha-(Trifluoromethylsulfonyloxy)hydrocinnamic acid methyl ester

Product 1

HCID 592167062-(5-Nitro-indol-1-yl)-3-phenyl-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 5-nitro-1H-indole (5.18 g, 31.93 mmol) in acetone (200 ml) at ambient temperature under a nitrogen atmosphere was added cesium carbonate (21.80 g, 67.06 mmol) followed by 3-phenyl-2-trifluoromethanesulfonyloxy-propionic acid methyl ester (10.96 g, 35.13 mmol). The resulting dark red mixture was stirred for 5 hours, concentrated in vacuo to a brown powder which was then partitioned between H2O (100 ml) and EtOAc (300 ml). All organics were combined, extracted with brine (250 ml), dried with MgSO4, filtered, and concentrated in vacuo. Gradient SiO2 chromatography (Hexane:EtOAc) afforded 2-(5-nitro-indol-1-yl)-3-phenyl-propionic acid methyl ester as an opaque syrup (5.91 g, 57% yield): MS (ESI) m/z 325, MS (ESI) m/z 323.

Workup

  1. concentrationconcentrated in vacuo to a brown powder which
  2. customwas then partitioned between H2O (100 ml) and EtOAc (300 ml)
  3. extractionextracted with brine (250 ml)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e44e252b26d04892bc29f7c29ccd6f71
Source dataset
uspto-grants-2010_03
Patent number
US07683091B2

Reaction notes

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