Triethylamine → 3-Amino-2-cyano-6-(trimethylsilylethynyl)pyridine

HRID 1734162Notes

Reaction equation

HRID 1734162 reaction equation
[NH2:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][C:5](I)=[CH:6][CH:7]=1.[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13].C(N(CC)CC)C>C(#N)C.[Cu](I)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>[NH2:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][C:5]([C:16]#[C:15][Si:12]([CH3:14])([CH3:13])[CH3:11])=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 190407853-Amino-2-cyano-6-iodopyridine

Product 1

HCID 190407873-Amino-2-cyano-6-(trimethylsilylethynyl)pyridine

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

This compound is prepared in a manner analogous to that of Step A of Example 9, using 3.8 grams (0,015 mole) of 3-amino-2-cyano-6-iodopyridine (prepared in Step A of Example 10), 2.1 grams (0.021 mole) of trimethylsilylacetylene, 10.6 mL of triethylamine, 0.13 gram of copper iodide, and 0.29 gram of bis(triphenylphosphine)palladium(II) chloride in 50 mL of acetonitrile, yielding 3-amino-2-cyano-6-(trimethylsilylethynyl)pyridine.

Workup

  1. customThis compound is prepared in a manner analogous to that of Step A of Example 9

Sources & evidence

ORD record
ord-ea585f1f53c3462995659d7176cba6d5
Source dataset
uspto-grants-1996_07
Patent number
US05532367

Reaction notes

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