Hydrochloric Acid → HCID 68883946, compound

HRID 1295045Notes

Reaction equation

HRID 1295045 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.[C:22]1([Mg]Br)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl>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]>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:7]2[C:6]3[C:10](=[C:2]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:3]=[CH:4][CH:5]=3)[N:9]([CH2:11][CH2:12][CH3:13])[N:8]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 68882935HCID 68882935, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 68883946HCID 68883946, compoundYield 59.2%

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 (0.600 g, 0.1.98 mmol) in anhydrous dioxane (8 mL) was added tris(dibenzylideneacetone)-dipalladium(0) (0.036 g, 0.04 mmol) and 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene HCl (0.036 g, 0.08 mmol). Phenylmagnesium bromide (1.18 mL, 3.56 mmol, 3M in diethyl ether) was added and the reaction heated to 80° C. for 3 hours. After this time an additional equivalent of reagents was added and the reaction heated for an additional 18 hours. The reaction mixture was treated with 1N aqueous hydrochloric acid solution and extracted with ethyl acetate. The organic layer washed with water and saturated aqueous sodium chloride solution. After drying over anhydrous magnesium sulfate, the organic phase was filtered and the filtrate evaporated in vacuo to yield crude title compound. The oil was purified by silica gel column chromatography eluting with hexane/ethyl acetate (5/1) to provide the title compound as a white solid (0.405 g, 1.18 mmol, 59%).

Workup

  1. additionAfter this time an additional equivalent of reagents was added
  2. temperaturethe reaction heated for an additional 18 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer washed with water and saturated aqueous sodium chloride solution
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. filtrationthe organic phase was filtered
  7. customthe filtrate evaporated in vacuo
  8. customto yield crude title compound
  9. customThe oil was purified by silica gel column chromatography
  10. washeluting with hexane/ethyl acetate (5/1)

Sources & evidence

ORD record
ord-0b29fabec890409bb2e7929e11e553e1
Source dataset
uspto-grants-2007_07
Patent number
US07241791B2

Reaction notes

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