Water → HCID 69333137, compound

HRID 915058Notes

Reaction equation

HRID 915058 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[N:10]=[C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:12]([C:16]2[CH:17]=[CH:18][C:19](=[O:23])[N:20]([CH3:22])[N:21]=2)=[N:13][C:14]=1Br.[C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)#[CH:31].O>CN(C=O)C.CC(C)=O.[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>[NH2:8][C:9]1[N:10]=[C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:12]([C:16]2[CH:17]=[CH:18][C:19](=[O:23])[N:20]([CH3:22])[N:21]=2)=[N:13][C:14]=1[C:31]#[C:30][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

9

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 86074880HCID 86074880, compound

Product 1

HCID 69333137HCID 69333137, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

In the presence of copper(I) iodide (4.3 mg) and dichlorobis(triphenylphosphine)palladium(II) (15.7 mg), triethylamine (0.0685 ml) was dropwise added to a mixture of 6-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-methyl-3(2H)-pyridazinone (150 mg) and ethynylbenzene (0.0054 ml) in DMF (1.5 ml) at 75-80° C. The mixture was stirred at the same temperature for 2 hours. To the reaction mixture, water was added to give a solid. The solid was purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (40:60 v/v) to give a solid. The solid was suspended in acetone to give 6-[5-amino-3-phenyl-6-(phenylethynyl)-2-pyrazinyl]-2-methyl-3(2H)-pyridazinone (96 mg).

Workup

  1. customto give a solid
  2. customThe solid was purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (40:60 v/v)
  3. customto give a solid

Sources & evidence

ORD record
ord-bcf00f8bcf814bd4a33f798ec32a48f3
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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