Triethylamine → HCID 57516792, compound

HRID 1966614Notes

Reaction equation

HRID 1966614 reaction equation
[Cl:1][C:2]1[CH:7]=NC(I)=C[N:3]=1.[F:9][C:10]1[CH:11]=[C:12]([C:16]#[CH:17])[CH:13]=[CH:14][CH:15]=1.[CH2:18]([N:20](CC)CC)[CH3:19]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[Cl:1][C:2]1[N:3]=[N:20][C:18]([C:17]#[C:16][C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([F:9])[CH:11]=2)=[CH:19][CH:7]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 5202181-Ethynyl-3-fluorobenzeneHCID 457896392-Chloro-5-iodopyrazine

Product 1

HCID 57516792HCID 57516792, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a well stirred solution of 2-chloro-5-iodopyrazine (600 mg, 2.5 mmol), 3-fluorophenyl-acetylene (315 mg, 303 μl, 2.62 mmol, 1.05 equiv.) in 7 ml of THF were added under argon atmosphere bis(triphenylphosphine)-palladium(II)dichloride (175 mg, 0.250 mmol, 0.02 equiv.), copper(I) iodide (23.8 mg, 0.125 mmol, 0.01 equiv.) and triethylamine (556 mg, 761 ul, 5.49 mmol, 2.2 equiv.). The mixture was stirred for 2 hours at room temperature. The crude mixture was filtered, adsorbed on silicagel and purified by flash chromatography over a 50 g silicagel column using a heptane to 25% ethyl acetate in heptane gradient. The title compound (450 mg, 78% yield) was obtained as a crystalline light-yellow solid, MS: m/e=233.1, 235.0 (M+H+).

Workup

  1. filtrationThe crude mixture was filtered
  2. custompurified by flash chromatography over a 50 g silicagel column

Sources & evidence

ORD record
ord-96a82d7552f6482d8089c8cab142ed56
Source dataset
uspto-grants-2013_04
Patent number
US08420661B2

Reaction notes

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