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Hydrochloric Acid → 3-(4-methoxyphenyl)-7-phenyl-2-propyl-2H-indazole

HRID 1295043
Notes
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Reaction equation

HRID 1295043 reaction equation
Cl[C:2]1[C:10]2[C:6](=[C:7]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:8]([CH2:11][CH2:12][CH3:13])[N:9]=2)[CH:5]=[CH:4][CH:3]=1.Cl.[C:23]1([Mg]Br)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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]>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:7]2[N:8]([CH2:11][CH2:12][CH3:13])[N:9]=[C:10]3[C:6]=2[CH:5]=[CH:4][CH:3]=[C:2]3[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:15][CH:16]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 688824767-chloro-3-(4-methoxyphenyl)-2-propyl-2H-indazoleHCID 178418255HCID 178418255, compound

Product 1

HCID 688851453-(4-methoxyphenyl)-7-phenyl-2-propyl-2H-indazoleYield 78.8%

Reagents, catalysts & solvents 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 7-Chloro-3-(4-methoxyphenyl)-2-propyl-2H-indazole (0.200 g, 0.66 mmol) in anhydrous dioxane (6 mL) was added tris(dibenzylideneacetone)-dipalladium(0) (0.0128 g, 0.013 mmol) and 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene.HCl (0.011 g, 0.07 mmol). Phenylmagnesium bromide (0.4 mL, 1.20 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 (0.178 g, 0.52 mmol, 78%).

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-93eb66b16f0a427d879199118c6cdf07
Source dataset
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07241791B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes