Triethylamine → 3-Amino-2-cyano-6-[(4-chlorophenyl)ethynyl]pyridine

HRID 440907Notes

Reaction equation

HRID 440907 reaction equation
[NH2:1][C:2]1[C:3]([C:10]#[N:11])=[N:4][C:5]([C:8]#[CH:9])=[CH:6][CH:7]=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16](I)=[CH:15][CH:14]=1.C(N(CC)CC)C>C(#N)C.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.[Cu](I)I>[NH2:1][C:2]1[C:3]([C:10]#[N:11])=[N:4][C:5]([C:8]#[C:9][C:16]2[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH:15]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 125101-Chloro-4-iodobenzeneHCID 190407883-Amino-6-ethynylpicolinonitrile

Product 1

HCID 190407863-Amino-2-cyano-6-[(4-chlorophenyl)ethynyl]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 C of Example 9, using 3.1 grams (0.022 mole) of 3-amino-2-cyano-6-ethynylpyridine, 7.4 grams (0.031 mole)of 4-chlorophenyl iodide, 10.7 grams (0.077 mole) of triethylamine, 0.5 gram (catalyst) of bis(triphenylphosphine)palladium(II) chloride, and 0.5 gram (catalyst) of copper iodide in 100 mL of acetonitrile, yielding 3-amino-2-cyano-6-[(4-chlorophenyl)ethynyl]pyridine.

Workup

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

Sources & evidence

ORD record
ord-26a1350104a644a6b580968881ad8708
Source dataset
uspto-grants-1996_05
Patent number
US05521190

Reaction notes

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