(E)-3-(4-Bromophenyl)-1-(pyridazin-4-yl)prop-2-en-1-one → HCID 86684795, compound

HRID 1527968Notes

Reaction equation

HRID 1527968 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[Mg]Br.[Br:10][C:11]1[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]([C:21]2[CH:26]=[CH:25][N:24]=[N:23][CH:22]=2)=[O:20])=[CH:13][CH:12]=1>O1CCCC1.[Cu]I>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH3:9])[CH2:18][C:19]([C:21]2[CH:26]=[CH:25][N:24]=[N:23][CH:22]=2)=[O:20])=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 86684794(E)-3-(4-Bromophenyl)-1-(pyridazin-4-yl)prop-2-en-1-oneHCID 178424303HCID 178424303, compound

Product 1

HCID 86684795HCID 86684795, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of copper(I) iodide (63.4 mg, 333 μmol) in tetrahydrofuran (10 ml) was added at 0° C. o-tolylmagnesium bromide solution (2 M in diethyl ether, 3.66 ml, 7.33 mmol) to give a light brown suspension. The reaction mixture was stirred at this temperature for 1½ h, then a solution of (E)-3-(4-bromophenyl)-1-(pyridazin-4-yl)prop-2-en-1-one (963 mg, 3.33 mmol) in THF (5.0 ml) was added, then after 1¾ h the reaction mixture was partitioned between sat. aq. ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2; ethyl acetate/heptane 1:1) afforded the title compound (809 mg, 64%). Light yellow foam; MS: 381.1 [M+H]+.

Workup

  1. customto give a light brown suspension
  2. customafter 1¾ h the reaction mixture was partitioned between sat. aq. ammonium chloride solution and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-8272fc30a3d9428c966b9ae49b93795c
Source dataset
uspto-grants-2015_07
Patent number
US09090565B2

Reaction notes

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