Potassium Carbonate → 1-benzenesulfonyl-3-(3,4-dimethoxy-phenyl)-1H-indole

HRID 1820880노트

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HRID 1820880 반응식
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](Br)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:25]3[CH:24]=[CH:23][C:22]([O:21][CH3:20])=[C:27]([O:28][CH3:29])[CH:26]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 27347023,4-Dimethoxyphenylboronic acidHCID 27762153-Bromo-(1-phenylsulfonyl)indole

생성물 1

HCID 578917491-benzenesulfonyl-3-(3,4-dimethoxy-phenyl)-1H-indole

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

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온도
120 °C

실험 절차

1-Benzenesulfonyl-3-bromoindole 20 (350 mg, 1.0 mmol) was dissolved in tetrahydrofuran (6 mL). Into the solution was added 3,4-dimethoxyphenyl boronic acid (379 mg, 2.1 mmol), tetrakis(triphenylphosphine)palladium(0) (60 mg, 0.05 mmol) and 1 M potassium carbonate (3 mL). The reaction mixture was heated in a CEM Discover microwave instrument at 120° C. for 10 minutes. The reaction mixture was concentrated under reduced pressure and partioned between ethyl acetate and saturated sodium bicabonate. The organic portion was dried over anhydrous magnesium sulfate, and filtered. The filtrate was adsorbed onto silica gel and purified by flash chromatography (5%-50% ethyl acetate:hexanes) to provide the desired product, 19, (359 mg, 88%).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dry with materialThe organic portion was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. custompurified by flash chromatography (5%-50% ethyl acetate:hexanes)

출처 및 근거

ORD 기록
ord-915151a8ef954ae7b85b773df75a1584
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07605168B2

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