HCID 68882935, compound → HCID 68882772, compound

HRID 1295028Notes

Reaction equation

HRID 1295028 reaction equation
Cl[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH2:12][CH3:13])[N:8]=[C:7]2[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([Mg]Br)=[CH:26][CH:25]=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:10]=2[N:9]([CH2:11][CH2:12][CH3:13])[N:8]=[C:7]3[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 68882935HCID 68882935, compoundHCID 178491912HCID 178491912, compound

Product 1

HCID 68882772HCID 68882772, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 7-chloro-3-(4-methoxyphenyl)-1-propyl-1H-indazole (0.10 g, 0.33 mmol) in anhydrous dioxane (3 mL) was added tris(dibenzylideneacetone)dipalladium(0) (0.004 g, 0.0043 mmol) and 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene HCl (0.0035 g, 0.0099 mmol). 4-Methoxyphenylmagnesium bromide (1.2 mL, 0.5M in diethyl ether) was added and the reaction mixture degassed. The reaction was heated to 80° C. for 18 hours. The reaction mixture was partitoned with 1N HCl and ethyl acetate. The organic layer was washed with water and brine. After drying (Na2SO4), the organic phase was concentrated in vacuo to yield crude title compound. The oil was purified by flash chromatography (silica gel, hexane/ethyl acetate, 5:1) to provide the title compound as a white solid (0.028 g).

Workup

  1. customthe reaction mixture degassed
  2. washThe organic layer was washed with water and brine
  3. dry with materialAfter drying (Na2SO4)
  4. concentrationthe organic phase was concentrated in vacuo
  5. customto yield crude title compound
  6. customThe oil was purified by flash chromatography (silica gel, hexane/ethyl acetate, 5:1)

Sources & evidence

ORD record
ord-bd240ac998e74291b6c8cf9c48620f05
Source dataset
uspto-grants-2007_07
Patent number
US07241791B2

Reaction notes

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