Trimethylsilylacetylene → HCID 71239905, compound

HRID 1403196Notes

Reaction equation

HRID 1403196 reaction equation
I[C:2]1[CH:3]=[C:4]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[O:9])[CH:5]=[CH:6][CH:7]=1.[C:17]([Si:19]([CH3:22])([CH3:21])[CH3:20])#[CH:18]>C(#N)C.CCOC(C)=O.[Cu]I>[CH3:16][N:13]1[CH2:14][CH2:15][N:10]([C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([C:18]#[C:17][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:3]=2)=[O:9])[CH2:11][CH2:12]1

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 3409622HCID 3409622, compound

Product 1

HCID 71239905HCID 71239905, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

(3-Iodophenyl)(4-methylpiperazin-1-yl)methanone (1.15 g, 3.5 mmol) and ethynyl-trimethyl-silane (0.58 mL, 4.2 mmol) in dry acetonitrile (30 mL) were purged with nitrogen and treated with TEA (0.97 mL, 7.0 mmol, 2 eq.), CuI (0.033 g, 0.17 mmol) and Pd (Ph3P)2Cl2 (0.120 g, 0.17 mmol). The reaction was stirred at room temperature for 2 h, then was diluted with EtOAc (30 mL), washed with water (2×20 mL), brine, dried over sodium sulphate, and evaporated. The crude was purified by flash chromatography on silica gel (DCM/MeOH 95/5) to afford the title compound (0.95 g, 91%).

Workup

  1. washwashed with water (2×20 mL), brine
  2. dry with materialdried over sodium sulphate
  3. customevaporated
  4. customThe crude was purified by flash chromatography on silica gel (DCM/MeOH 95/5)

Sources & evidence

ORD record
ord-1ac8faaf21a54dad9b1f4a011cab209c
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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