Sodium Carbonate → 4-[6-(4-Cyano-phenyl)-2-oxo-2,3-dihydro-indol-1-ylmethyl]-N,N-dimethyl-benzenesulfonamide

HRID 1355660노트

반응식

HRID 1355660 반응식
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:24])[N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([S:18]([N:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:31]([C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1)#[N:32]>C1(C)C=CC=CC=1.CCO.O.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:31]([C:33]1[CH:38]=[CH:37][C:36]([C:2]2[CH:10]=[C:9]3[C:5]([CH2:6][C:7](=[O:24])[N:8]3[CH2:11][C:12]3[CH:17]=[CH:16][C:15]([S:18]([N:21]([CH3:23])[CH3:22])(=[O:19])=[O:20])=[CH:14][CH:13]=3)=[CH:4][CH:3]=2)=[CH:35][CH:34]=1)#[N:32]

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 185077814-(6-Bromo-2-oxo-2,3-dihydro-indol-1-ylmethyl)-n,n-dimethyl-benzenesulfonamide

생성물 1

HCID 185077664-[6-(4-Cyano-phenyl)-2-oxo-2,3-dihydro-indol-1-ylmethyl]-N,N-dimethyl-benzenesulfonamide수율 63%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

4-(6-Bromo-2-oxo-2,3-dihydro-indol-1-ylmethyl)-N,N-dimethyl-benzenesulfonamide (1.60 g, 4.24 mmol) and tetrakis(triphenylphosphine)palladium (0) (195 mg, 0.17 mmol) were dissolved in a solution of 25 ml of toluene and 4 ml of EtOH under an atmosphere of dry N2. To the reaction mixture was added a solution of aqueous sodium carbonate (Na2CO3) (1.03 g, 9.75 mmol) dissolved in 6 ml of water followed by 4-cyanobenzene boronic acid (1.55 g, 10.6 mmol). The reaction mixture was heated to 100° C. and stirred at this temperature overnight. The reaction mixture was concentrated under vacuum and then partitioned between DCM and saturated aqueous NaHCO3. The DCM layer was dried over MgSO4, filtered and concentrated under vacuum to give a brown oil. The brown oil was chromatographed on silica gel eluting with a gradient from DCM to DCM/MeOH (98:2) to give 1.15 g of the titled compound as an orange solid in 63% yield.

후처리

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. custompartitioned between DCM and saturated aqueous NaHCO3
  3. dry with materialThe DCM layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto give a brown oil
  7. customThe brown oil was chromatographed on silica gel eluting with a gradient from DCM to DCM/MeOH (98:2)

출처 및 근거

ORD 기록
ord-0a3503d8aa0d47cb8060a66314cfcc6c
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586447B1

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