1,2-Dimethoxyethane → HCID 68882090, compound

HRID 1295032Notes

Reaction equation

HRID 1295032 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(COC)OC.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.CC(C)([O-])C.[Na+]>O>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:7]2[C:6]3[C:10](=[C:2]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]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 4

HCID 80711,2-DimethoxyethaneHCID 8083MorpholineHCID 23676156Sodium t-butoxideHCID 68882935HCID 68882935, compound

Product 1

HCID 68882090HCID 68882090, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 7-chloro-3-(4-methoxyphenyl)-1-propyl-1H-indazole (0.218 g, 0.73 mmol) in anhydrous degassed dimethoxyethane (3 mL) was added morpholine (0.076 mL, 0.84 mmol) and sodium t-butoxide (0.098 g, 1.02 mmol). Tris(dibenzylidene-acetone)dipalladium(0) (0.010 g, 0.011 mmol) and 2-dicyclohexyl phosphino-2′-(N,N-dimethylamino)biphenyl (0.09 g, 0.23 mmol) were added and the reaction refluxed for 90 minutes. The reaction was cooled to room temperature and water added. The mixture was extracted with ethyl acetate and 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 3/1) to provide the title compound as a white solid (0.157 g, 0.45 mmol, 63%). An analytical sample was crystallized from hexane.

Workup

  1. temperaturethe reaction refluxed for 90 minutes
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layer washed with water and saturated aqueous sodium chloride solution
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. filtrationthe organic phase was filtered
  6. customthe filtrate evaporated in vacuo
  7. customto yield crude title compound
  8. customThe oil was purified by silica gel column chromatography
  9. washeluting with hexane/ethyl acetate (5/1 to 3/1)

Sources & evidence

ORD record
ord-fa0727082f244d919271a959ba082402
Source dataset
uspto-grants-2007_07
Patent number
US07241791B2

Reaction notes

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