Trimethylsilylacetylene → HCID 66922255, compound

HRID 2039859Notes

Reaction equation

HRID 2039859 reaction equation
Cl[C:2]1[C:7]([NH2:8])=[CH:6][C:5]([CH3:9])=[CH:4][N:3]=1.[CH3:10][Si:11]([C:14]#[CH:15])([CH3:13])[CH3:12]>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>[CH3:9][C:5]1[CH:6]=[C:7]([NH:8][C:15]#[C:14][Si:11]([CH3:13])([CH3:12])[CH3:10])[CH:2]=[N:3][CH:4]=1

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 27344222-Chloro-5-methylpyridin-3-amine

Product 1

HCID 66922255HCID 66922255, compoundYield 35.7%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
80 °C

Procedure

2-Chloro-5-methyl-pyridin-3-ylamine (10 g, 70.13 mmol), trimethylsilylacetylene (13.8 g, 140.3 mmol), copper(I) iodide (534 mg, 2.81 mmol) and bis(triphenylphosphine)palladium(II) chloride (1.97 g, 2.81 mmol) were dissolved in triethylamine (140 ml) and stirred at 80° C. for 5 h. After cooling to room temperature, the reaction mixture was filtered over a plug of celite, and the solvent was removed in vacuo. The residue was purified by column chromatography (silica gel, EA/HEP) to give 5.12 g of the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered over a plug of celite
  3. customthe solvent was removed in vacuo
  4. customThe residue was purified by column chromatography (silica gel, EA/HEP)

Sources & evidence

ORD record
ord-efe8b41371f1471781f60d3a5db32980
Source dataset
uspto-grants-2013_11
Patent number
US08580813B2

Reaction notes

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