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

HRID 1355660ノート

反応式

HRID 1355660 の反応式
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]

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-0a3503d8aa0d47cb8060a66314cfcc6c
出典データセット
uspto-grants-2003_07
特許番号
US06586447B1

反応ノート

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