Water → 3-(2-Methylindol-4-yl)acrylic Acid Methyl Ester

HRID 11412Notes

Reaction equation

HRID 11412 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1OS(O)(=O)=O)=[C:8]([C:16](F)(F)F)[CH:7]=[CH:6][CH:5]=2.[CH3:20][O:21][C:22](=[O:25])[CH:23]=C.C(N(C(C)C)CC)(C)C.O>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C>[CH3:20][O:21][C:22](=[O:25])[CH:23]=[CH:16][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[C:2]([CH3:1])[NH:3]2

Participants

8

Reactant 4

HCID 962WaterHCID 7294Methyl AcrylateHCID 81531DiisopropylethylamineHCID 21974497HCID 21974497, compound

Product 1

HCID 695893183-(2-Methylindol-4-yl)acrylic Acid Methyl Ester

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

To a solution 2-methyl-4-trifluoromethylsulfoxyindole (3.2 g; prepared in Reference Example 2) in N,N-dimethylformamide (50 ml) was added acrylic acid methyl ester (2.24 ml), diisopropylethylamine (5.9 ml) and dichlorobis(triphenylphosphine)palladium(II) (238 mg), and the mixture was stirred at 95° C. for 2 days. To the reaction mixture was added water and ethyl acetate, then separated. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and a saturated aqueous solution of sodium chloride, successively, dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane-ethyl acetate) to give the title compound (950 mg) having the following physical data.

Workup

  1. customseparated
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layer was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, successively, dried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-1894c7f70c5c4391b585a4d47e964011
Source dataset
uspto-grants-2006_08
Patent number
US07098234B2

Reaction notes

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