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

HRID 1355660Notes

Reaction equation

HRID 1355660 reaction equation
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]

Participants

8

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-0a3503d8aa0d47cb8060a66314cfcc6c
Source dataset
uspto-grants-2003_07
Patent number
US06586447B1

Reaction notes

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