Diethylamine → 3-[3-(2-diethylamino-ethyl)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one

HRID 1829054Notes

Reaction equation

HRID 1829054 reaction equation
[O:1]=[C:2]1[C:10](=[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]([CH2:20][CH2:21]OS(C)(=O)=O)[O:12]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[CH2:27]([NH:29][CH2:30][CH3:31])[CH3:28].O1CCOCC1>C1COCC1>[CH2:27]([N:29]([CH2:30][CH3:31])[CH2:21][CH2:20][CH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11](=[C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[NH:3][C:2]2=[O:1])[O:12]1)[CH3:28]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 312751,4-DioxaneHCID 72382355Methanesulfonic Acid 2-[3-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-1-yl]-ethyl Ester

Product 1

HCID 696592283-[3-(2-diethylamino-ethyl)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-oneYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methanesulfonic acid 2-[3-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-1-yl]-ethyl ester (50 mg, 0.135 mmol) and diethylamine (279 μl, 2.7 mmol) in THF (0.8 ml) was heated at 60° C. After 3 hours, dioxane (0.3 ml) was added to give a solution and the reaction continued at 60° C. for 24 h. The reaction was partitioned between EtOAc and water. The EtOAc layer was washed with water, brine, dried with anhydrous Na2SO4 and rotary evaporated to give brown oil. The brown oil was chromatographed (CHCl3 to 2% MeOH/CHCl3 gradient) to yield 3-[3-(2-diethylamino-ethyl)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one as a yellow-green solid (33 mg, 71%).

Workup

  1. customto give a solution
  2. waitthe reaction continued at 60° C. for 24 h
  3. customThe reaction was partitioned between EtOAc and water
  4. washThe EtOAc layer was washed with water, brine
  5. dry with materialdried with anhydrous Na2SO4
  6. customrotary evaporated
  7. customto give brown oil
  8. customThe brown oil was chromatographed (CHCl3 to 2% MeOH/CHCl3 gradient)

Sources & evidence

ORD record
ord-b82f502a9b71451797c94ced6f5ca5f7
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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