Morpholine → 3-[3-(2-morpholin-4-yl-ethyl)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one

HRID 1829053Notes

Reaction equation

HRID 1829053 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.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>O1CCOCC1>[N:27]1([CH2:21][CH2:20][CH:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:11](=[C:10]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[NH:3][C:2]3=[O:1])[O:12]2)[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 72382355Methanesulfonic Acid 2-[3-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-1-yl]-ethyl Ester

Product 1

HCID 696593573-[3-(2-morpholin-4-yl-ethyl)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-oneYield 76%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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 morpholine (118 μl, 1.35 mmol) in dioxane (0.8 ml) was heated at 70° C. for 40 minutes and then at 60° C. for 18 hours. 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 a yellow film. The yellow film was chromatographed (CHCl3 to 2% MeOH/CHCl3 gradient) to give 3-[3-(2-morpholin-4-yl-ethyl)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one as a yellow solid (37 mg, 76%).

Workup

  1. customThe reaction was partitioned between EtOAc and water
  2. washThe EtOAc layer was washed with water, brine
  3. dry with materialdried with anhydrous Na2SO4
  4. customrotary evaporated
  5. customto give a yellow film
  6. customThe yellow film was chromatographed (CHCl3 to 2% MeOH/CHCl3 gradient)

Sources & evidence

ORD record
ord-347573dadf11490a9a698a3ba50afbd4
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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