Trimethylsilylacetylene → 2-(4-Chloro-2-(2-(trimethylsilyl)ethynyl)phenyl)propanenitrile

HRID 1868848Notes

Reaction equation

HRID 1868848 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:11])[C:9]#[N:10])=[C:4](I)[CH:3]=1.[CH3:13][Si:14]([C:17]#[CH:18])([CH3:16])[CH3:15]>[Cu]I.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>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:11])[C:9]#[N:10])=[C:4]([C:18]#[C:17][Si:14]([CH3:16])([CH3:15])[CH3:13])[CH:3]=1

Participants

5

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 670999922-(4-Chloro-2-iodophenyl)propanenitrile

Product 1

HCID 670996472-(4-Chloro-2-(2-(trimethylsilyl)ethynyl)phenyl)propanenitrile

Reagents, catalysts & solvents 2

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

Procedure

2-(4-Chloro-2-iodophenyl)propanenitrile (0.620 g, 2.13 mmol), (trimethylsilyl)acetylene (0.451 mL, 3.19 mmol), copper(I) iodide (0.0144 mL, 0.425 mmol), dichlorobis(triphenylphosphine)palladium (II) (0.149 g, 0.213 mmol), and TEA (20 mL) were stirred at 70° C. for 3 hours. The reaction was monitored by LC-MS. The solution was filtered through a plug of Celite, and the filtrate was concentrated under vacuum. The residue was purified by silica flash chromatography, 0-15% EtOAc/hexanes. MS m/e=262 (M+H)+.

Workup

  1. filtrationThe solution was filtered through a plug of Celite
  2. concentrationthe filtrate was concentrated under vacuum
  3. customThe residue was purified by silica flash chromatography, 0-15% EtOAc/hexanes

Sources & evidence

ORD record
ord-527202cb2377412b95a127efcfa96399
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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