p-Ethynyltoluene → N-(4-p-Tolylethynyl-phenyl)-methanesulfonamide

HRID 1716302Notes

Reaction equation

HRID 1716302 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=1.[C:13]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)#[CH:14]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:18]1([CH3:21])[CH:19]=[CH:20][C:15]([C:13]#[C:14][C:2]2[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 13018p-EthynyltolueneHCID 836147N-(4-iodophenyl)methanesulfonamide

Product 1

HCID 68511472N-(4-p-Tolylethynyl-phenyl)-methanesulfonamide

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

A mixture of N-(4-iodo-phenyl)-methanesulfonamide (0.46 g, 1.54 mmol), Pd(PPh3)2Cl2 (54 mg, 0.077 mmol) and CuI (14.7 mg, 0.077 mmol) in TEA/THF (10 mL/3 mL) was treated with 1-ethynyl-4-methyl-benzene (0.29 mL, 2.32 mmol). The reaction mixture was degassed and stirred at room temperature for 30 min. The solvent was removed under the reduced pressure. The residue was diluted with EtOAc and water. After the usual work-up, the obtained crude material was purified by chromatography (35% EtOAc/hexanes) to give the desired product. MS (EI) 286 (M+H)+.

Workup

  1. customThe reaction mixture was degassed
  2. customThe solvent was removed under the reduced pressure
  3. additionThe residue was diluted with EtOAc and water
  4. customAfter the usual work-up, the obtained crude material
  5. customwas purified by chromatography (35% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ea964cb07ad841b485d353a6aeb19a31
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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