Dichloromethane → 2-Bromo-5-(4-[1,2,3]triazol-1-yl-but-1-ynyl)-pyrazine

HRID 349242Notes

Reaction equation

HRID 349242 reaction equation
[Br:1][C:2]1[CH:7]=[N:6][C:5](I)=[CH:4][N:3]=1.[CH2:9]([N:13]1[CH:17]=[CH:16][N:15]=[N:14]1)[CH2:10][C:11]#[CH:12].C(N(CC)CC)C.ClCCl>CN(C=O)C.[Cu](I)I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:7]=[N:6][C:5]([C:12]#[C:11][CH2:10][CH2:9][N:13]2[CH:17]=[CH:16][N:15]=[N:14]2)=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 184535221-But-3-ynyl-1H-[1,2,3]triazoleHCID 219312002-Bromo-5-iodopyrazine

Product 1

HCID 442259082-Bromo-5-(4-[1,2,3]triazol-1-yl-but-1-ynyl)-pyrazine

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

2-Bromo-5-iodo-pyrazine (13.69 g, 48.0 mmol), 1-but-3-ynyl-1H-[1,2,3]triazole (7.01 g, 57.9 mmol) and triethyl amine (NEt3) (94 ml) are dissolved in DMF (188 ml) and copper iodide (CuI) (0.984 g, 5.17 mmol) is added under stirring. After passing a stream of argon through the mixture for 10 min tetrakis(triphenylphosphine)palladium(0) (2.844 g, 2.46 mmol) is added and stirring is continued for 5 h at r.t. Dichloromethane (300 ml) is added; the mixture is washed with 0.5N hydrochloric acid (HCl) and brine, dried over Na2SO4 and concentrated in vacuo. The crude product is purified by flash column chromatography (ethyl acetate/hexanes 7:3) yielding 2-bromo-5-(4-[1,2,3]triazol-1-yl-but-1-ynyl)-pyrazine as a colorless solid. Yield 9.99 g (75%).

Workup

  1. customfor 10 min
  2. additionis added
  3. stirringstirring
  4. washthe mixture is washed with 0.5N hydrochloric acid (HCl) and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by flash column chromatography (ethyl acetate/hexanes 7:3)

Sources & evidence

ORD record
ord-7dbb40d292d64f68bd4c712d82733e30
Source dataset
uspto-grants-2007_02
Patent number
US07179812B2

Reaction notes

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