Hydrochloric Acid → HCID 68883745, compound

HRID 1295041Notes

Reaction equation

HRID 1295041 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])=[C:16]([F:22])[CH:15]=1.[C:23]1([Mg]Br)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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]>[F:22][C:16]1[CH:15]=[C:14]([C:7]2[C:6]3[C:10](=[C:2]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:3]=[CH:4][CH:5]=3)[N:9]([CH2:11][CH2:12][CH3:13])[N:8]=2)[CH:19]=[CH:18][C:17]=1[O:20][CH3:21]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 68884326HCID 68884326, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 68883745HCID 68883745, compoundYield 66.1%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 7-chloro-3-(3-fluoro-4-methoxyphenyl)-1-propyl-1H-indazole (0.38 g, 1.18 mmol) in anhydrous dioxane (6 mL) was added tris(dibenzylideneacetone)-dipalladium(0) (0.022 g, 0.024 mmol) and 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene HCl (0.02 g, 0.047 mmol). Phenylmagnesium bromide (0.71 mL, 1.40 mmol, 2M in diethyl ether) was added and the reaction heated to 80° C. for 18 hours. The reaction mixture was treated with 1 N 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 (3/1) to provide the title compound as a white solid (0.28 g, 0.78 mmol, 66%). This material was used directly in step 2.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer washed with water and saturated aqueous sodium chloride solution
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. filtrationthe organic phase was filtered
  5. customthe filtrate evaporated in vacuo
  6. customto yield crude title compound
  7. customThe oil was purified by silica gel column chromatography
  8. washeluting with hexane/ethyl acetate (3/1)

Sources & evidence

ORD record
ord-65fea62255d447deb34cfbb7634cb0a3
Source dataset
uspto-grants-2007_07
Patent number
US07241791B2

Reaction notes

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