Triethylamine → 1-Phenylsulfonyl-5-trimethylsilylethynylindole

HRID 352768노트

반응식

HRID 352768 반응식
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:6]=[CH:5]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[CH3:46][Si:47]([C:50]#[CH:51])([CH3:49])[CH3:48]>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(OCC)(=O)C.CN(C)C=O>[C:14]1([S:11]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([C:51]#[C:50][Si:47]([CH3:49])([CH3:48])[CH3:46])=[CH:10][CH:9]=3)[CH:5]=[CH:6]2)(=[O:13])=[O:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

10

반응물 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 27762101-(Benzenesulfonyl)-5-bromo-1H-indole

생성물 1

HCID 227101661-Phenylsulfonyl-5-trimethylsilylethynylindole

시약·촉매·용매 5

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

In tetrahydrofuran (7.00 ml), 5-bromo-1-phenylsulfonylindole (1.50 g) and triphenylphosphine (351 mg) were dissolved. Triethylamine (20 ml), N,N-dimethylformamide (7.00 ml), trimethylsilylacetylene (945 up) and palladium acetate (100 mg) were added to the resulting solution at room temperature, followed by heating under reflux for 5 hours. After the reaction mixture was allowed to cool down to room temperature, ethyl acetate and water were added to the reaction mixture to separate the organic layer. The resulting organic layer was dried over anhydrous sodium sulfate and then distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=20:1 to 10:1), whereby the title compound (935 mg, 59%) was obtained as a white solid.

후처리

  1. temperatureby heating
  2. temperatureunder reflux for 5 hours
  3. customto separate the organic layer
  4. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=20:1 to 10:1), whereby the title compound (935 mg, 59%)
  8. customwas obtained as a white solid

출처 및 근거

ORD 기록
ord-fcfe8dd1bb1e435ab49ee672503ac59c
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06747023B1

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