5-fluoro-1,3-dihydro-2H-indol-2-one → HCID 68997207, compound

HRID 1254937Notes

Reaction equation

HRID 1254937 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.[OH:27][CH:28]1[CH2:33][CH2:32][N:31]([CH2:34][CH2:35][C:36]2[CH:37]=[C:38]3[C:42](=[CH:43][CH:44]=2)[C:41](=O)[O:40][C:39]3([CH3:47])[CH3:46])[CH2:30][CH2:29]1>C1COCC1>[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:41]1[C:42]2[C:38](=[CH:37][C:36]([CH2:35][CH2:34][N:31]3[CH2:32][CH2:33][CH:28]([OH:27])[CH2:29][CH2:30]3)=[CH:44][CH:43]=2)[C:39]([CH3:47])([CH3:46])[O:40]1

Participants

5

Reactant 3

HCID 37310125-fluoro-1,3-dihydro-2H-indol-2-oneHCID 23714775LiHMDS tetrahydrofuranHCID 58586240HCID 58586240, compound

Product 1

HCID 68997207HCID 68997207, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-fluorooxindole (7.86 g, 52 mmol) in anhydrous THF (60 ml) under nitrogen was added 1.0M LiHMDS/THF solution (104 ml, 104 mmol). The mixture was stirred at room temperature for 15 minutes, and then 5-[2-(4-hydroxy-piperidin-1-yl)-ethyl]-3,3-dimethyl-3H-isobenzofuran-1-one (5.0 g, 17.3 mmol) was added. After stirring at room temperature for 2 hours, the mixture was quenched with 50 ml of 2.5M H2SO4, heated at 65° C. for 30 minutes and poured into 500 ml of water. The mixture was basified with 5M NaOH to about pH=9 and continuously stirred at room temperature for 16 hours. The resulting solids were filtered, rinsed with water, dried under vacuum to give the title compound as a yellow solid (4.74 g, 65%).

Workup

  1. stirringAfter stirring at room temperature for 2 hours
  2. customthe mixture was quenched with 50 ml of 2.5M H2SO4
  3. temperatureheated at 65° C. for 30 minutes
  4. additionpoured into 500 ml of water
  5. stirringcontinuously stirred at room temperature for 16 hours
  6. filtrationThe resulting solids were filtered
  7. washrinsed with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-92b361d5a31e42f8bae1a9090bb6ecdd
Source dataset
uspto-grants-2013_06
Patent number
US08455656B2

Reaction notes

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