Trimethylsilylacetylene → HCID 178433225, compound

HRID 428733Notes

Reaction equation

HRID 428733 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])/[C:5]/2=[CH:12]\[C:13]1[NH:17][CH:16]=[N:15][C:14]=1[CH3:18].[CH3:19][Si:20]([C:23]#[CH:24])([CH3:22])[CH3:21]>CN(C=O)C.C(N(CC)CC)C.[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>[CH3:18][C:14]1[N:15]=[CH:16][NH:17][C:13]=1/[CH:12]=[C:5]1\[C:6](=[O:11])[NH:7][C:8]2[C:4]\1=[CH:3][C:2]([C:24]#[C:23][Si:20]([CH3:22])([CH3:21])[CH3:19])=[CH:10][CH:9]=2

Participants

7

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 178433222HCID 178433222, compound

Product 1

HCID 178433225HCID 178433225, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

(Z)-5-Bromo-1,3-dihydro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one (0.17 g, 0.56 mmol) (from Example 99) was dissolved in 3 mL DMF and 3 mL triethylamine. The solution was degassed for 30 minutes by bubbling argon through the solution. At this time (trimethylsilyl)acetylene (0.3 mL, 2.1 mmol) (Aldrich), CuI (34 mg) (Aldrich) and (Ph3P)2PdCl2 (34 mg) (Aldrich) were added and the reaction flask sealed. The reaction was heated, under argon, at 90° C. for 18 hours. After cooling, the mixture was filtered through Celite® (Fisher Scientific) and residue washed extensively with hot EtOAc and CH3CN. Combined filtrate and washing was concentrated under reduced pressure and the product was purified via flash column chromatography (SiO2, 230-400 mesh) with 5% MeOH in CH2Cl2. (Yield 0.1 g, 56%).

Workup

  1. customThe solution was degassed for 30 minutes
  2. customby bubbling argon through the solution
  3. customthe reaction flask sealed
  4. temperatureAfter cooling
  5. filtrationthe mixture was filtered through Celite® (Fisher Scientific) and residue
  6. washwashed extensively with hot EtOAc and CH3CN
  7. washCombined filtrate and washing
  8. concentrationwas concentrated under reduced pressure
  9. customthe product was purified via flash column chromatography (SiO2, 230-400 mesh) with 5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-3da9fde8f87546d3b3931e7f3e89a041
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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