Diethyl Ether → 4-((Trimethylsilyl)ethynyl)benzenesulfonamide

HRID 854933Notes

Reaction equation

HRID 854933 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:12]([Si:14]([CH3:17])([CH3:16])[CH3:15])#[CH:13].C(OCC)C>C1(C)C=CC=CC=1.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.[Cu]I>[CH3:15][Si:14]([C:12]#[C:13][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1)([CH3:17])[CH3:16]

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 66111TrimethylsilylacetyleneHCID 696964-Bromobenzenesulfonamide

Product 1

HCID 695174394-((Trimethylsilyl)ethynyl)benzenesulfonamideYield 61%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalyst2×HCID 1140TolueneSolvent

Procedure

To a solution of 4-bromobenzenesulfonamide (4.51 g, 19.1 mmole) in toluene (900 mL) at 75° C. was added ethynyl(trimethyl)silane (4 g, 40 mmole), Pd(PPh3)4 (1.3 g, 1.1 mmole), CuI (0.46 g, 2.42 mmole) and TEA (5.7 g, 56 mmole) and the mixture was allowed to cool to room temperature while stirring. Additional Pd(PPh3)4 (1 g, 0.9 mmole) was added and the mixture was stirred at room temperature. After 5 days, ethyl ether was added and the mixture was washed with 10% HCl, H2O, sat. aqueous NH4Cl, dried over Na2SO4 and concentrated in vacuo to give 2.93 g (61% yield) of the product: ESHRMS m/z 271.0935 (M+NH4, C11H15NO2SSiNH4, Calc'd 271.0937).

Workup

  1. stirringthe mixture was stirred at room temperature
  2. washthe mixture was washed with 10% HCl, H2O, sat. aqueous NH4Cl
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e038fba1a464a9d973e1f77b50c97f5
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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