2,3-Dichloropyrazine → HCID 59177859, compound

HRID 1875445Notes

Reaction equation

HRID 1875445 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=1.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]#[CH:17]>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>[Cl:8][C:7]1[C:2]([C:17]#[C:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[F:9])=[N:3][CH:4]=[CH:5][N:6]=1

Participants

6

Reactant 2

HCID 785752,3-DichloropyrazineHCID 6433581-Ethynyl-2-fluorobenzene

Product 1

HCID 59177859HCID 59177859, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
0 °C

Procedure

49 mg (0.26 mmol) of copper(I) iodide and 179 mg (0.26 mmol) of bis(triphenyl-phosphine)palladium(II) chloride are added to a solution of 760 mg (5.10 mmol) of 2,3-dichloropyrazine in 27 ml of triethylamine and cooled to 0° C. Then 919 mg (7.65 mmol) of 2-fluoro-phenylacetylene are added dropwise, and the mixture is heated at 80° C. for 3 h. It is then filtered and concentrated. The residue is purified by preparative HPLC. 717 mg (60% of theory) of the title compound are obtained as pale beige crystals.

Workup

  1. temperaturethe mixture is heated at 80° C. for 3 h
  2. filtrationIt is then filtered
  3. concentrationconcentrated
  4. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-4252ff979c4344ef9fe2a9d9bf18f291
Source dataset
uspto-grants-2012_11
Patent number
US08309551B2

Reaction notes

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