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

HRID 351645노트

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HRID 351645 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
95 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-456b150452784242b8c8155b14531d7f
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743793B2

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