Sulfuric Acid → HCID 68997976, compound

HRID 1254940Notes

Reaction equation

HRID 1254940 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1.O=[C:28]1[C:36]2[C:31](=[CH:32][C:33]([CH2:37][CH2:38][C:39]([OH:41])=[O:40])=[CH:34][CH:35]=2)[CH2:30][O:29]1.S(=O)(=O)(O)O>C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[C:28]1[C:36]2[C:31](=[CH:32][C:33]([CH2:37][CH2:38][C:39]([OH:41])=[O:40])=[CH:34][CH:35]=2)[CH2:30][O:29]1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 37310125-fluoro-1,3-dihydro-2H-indol-2-oneHCID 23714775LiHMDS tetrahydrofuranHCID 58586311HCID 58586311, compound

Product 1

HCID 68997976HCID 68997976, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-fluorooxindole (218 mg, 1.44 mmol) in anhydrous THF (10 ml) under nitrogen was added 1.0M LiHMDS/THF solution (2.9 ml, 2.9 mmol). After the mixture was stirred at room temperature for 10 minutes, 3-(1-Oxo-1,3-dihydro-isobenzofuran-5-yl)-propionic acid (100 mg, 0.48 mmol) was added. After the mixture was stirred at room temperature for 2 hours, 1 M sulfuric acid solution (10 ml) was added. The mixture was heated at 60° C. for 2 hours, and then poured into 150 ml of water. The resulting solid was filtered, rinsed with water, dried in vacuo to give the title compound as a yellow solid (96 mg, 59%).

Workup

  1. stirringAfter the mixture was stirred at room temperature for 2 hours
  2. temperatureThe mixture was heated at 60° C. for 2 hours
  3. filtrationThe resulting solid was filtered
  4. washrinsed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-be33d0eefb07496a96ef3cd8d40ed5c9
Source dataset
uspto-grants-2013_06
Patent number
US08455656B2

Reaction notes

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