Triethylamine → HCID 18376030, compound

HRID 2300200Notes

Reaction equation

HRID 2300200 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.[C:9]1([C:15]#[CH:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C>O.[Cu]I>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([C:16]#[C:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:3][CH:4]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 276852,5-Dichloropyridine

Product 1

HCID 18376030HCID 18376030, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Procedure

A mixture of 2,5 dichloropyridine (3.7 g, 25 mmol), phenylacetylene (3.02 ml, 1.1 eq), bis triphenylphosphine palladium dichloride (II) (Aldrich, 500 mg), copper (I) iodide (250 mg) and triethylamine (50 ml) was heated to reflux under N2 for 18 h. The cooled reaction mixture was diluted with water, extracted with diethyl ether, dried and concentrated to a black oil which was partially purified by SPE Si chromatography with gradient elution cyclohexane:ethyl acetate (100:0 to 10:1) gave the title compound as a brown solid (1.94 g, 36%). MH+ 213; 1H NMR (CDCl3) δ 7.37 (3H, m); 7.48 (1H, d, J 8 Hz); 7.59 (2H, m); 7.67 (1H, dd, J 8 & 2 Hz); 8.57 (1H, d, J 2 Hz); TLC SiO2 Cyclohexane: ethyl acetate (15:1) Rf 0.36.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2 for 18 h
  3. customThe cooled reaction mixture
  4. extractionextracted with diethyl ether
  5. customdried
  6. concentrationconcentrated to a black oil which
  7. customwas partially purified by SPE Si chromatography with gradient elution cyclohexane:ethyl acetate (100:0 to 10:1)

Sources & evidence

ORD record
ord-5152c6905a9f4298b133805a524f9569
Source dataset
uspto-grants-2002_12
Patent number
US06498166B1

Reaction notes

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