Potassium Carbonate → 1-benzenesulfonyl-3-(3,4-dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1820876

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HRID 1820876 반응식
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]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:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]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 455881343-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 578917891-benzenesulfonyl-3-(3,4-dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

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온도
120 °C

실험 절차

1-Benzenesulfonyl-3-bromo-1H-pyrrolo[2,3-b]pyridine (4, 1.00 g, 2.96 mmol) was dissolved in tetrahydrofuran (16 mL) and 3,4-dimethoxyphenyl boronic acid (1.35 g, 7.41 mmol), tetrakis(triphenylphosphine)palladium(0) (200 mg, 0.1 mmol), and 1 M potassium carbonate (8 mL) were added. The reaction mixture was heated in a CEM Discover microwave at 120° C. for 10 minutes. The reaction mixture was concentrated under reduced pressure and partitioned between ethyl acetate and water. The organic portions were dried with anhydrous magnesium sulfate, filtered, and the filtrate was adsorbed onto silica. The mixture was purified by flash chromatography (30% ethyl acetate:hexanes) to provide the desired product, 5, (909 mg, 78%). MS(ESI) [M+H+]+=394.9.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe organic portions were dried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe mixture was purified by flash chromatography (30% ethyl acetate:hexanes)

출처 및 근거

ORD 기록
ord-cd4a665d843e4f7793eede53cb126882
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07605168B2

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