Ammonium Chloride → 3-Hydroxy-5-(3,5-dimethylisoxazol-4-yl)-3-(2-(morpholinomethyl)phenyl)indolin-2-one

HRID 513250Notes

Reaction equation

HRID 513250 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[C:10]3=[O:17])=[C:5]([CH3:18])[O:4][N:3]=1.[N:19]1([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[Mg]Br)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.[Cl-].[NH4+]>C1COCC1>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[C:10]3([OH:17])[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[CH2:25][N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)=[C:5]([CH3:18])[O:4][N:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 1175999855-(3,5-Dimethylisoxazol-4-yl)indoline-2,3-dioneHCID 178419624HCID 178419624, compound

Product 1

HCID 862961023-Hydroxy-5-(3,5-dimethylisoxazol-4-yl)-3-(2-(morpholinomethyl)phenyl)indolin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(3,5-Dimethyl-isoxazol-4-yl)-1H-indole-2,3-dione (100 mg, 0.41 mmol) is dissolved in anhydrous THF (1 mL) and cooled to 0° C. (2-(4-Morpholinylmethyl)phenyl)magnesium bromide (4.0 mL, 1.0 mmol) is added dropwise and then the mixture stirred at room temperature for 2 hours. The mixture is poured onto saturated aqueous ammonium chloride solution. The aqueous phase is extracted with ethyl acetate. The organic phase is dried over magnesium sulfate. The solvent is concentrated to dryness and purified using column chromatography on silica gel using a cyclohexane/ethyl acetate gradient. The product fractions are combined and concentrated to dryness in vacuo.

Workup

  1. additionis added dropwise
  2. extractionThe aqueous phase is extracted with ethyl acetate
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. concentrationThe solvent is concentrated to dryness
  5. custompurified
  6. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-b845e6bd60b1476c987a36214334da19
Source dataset
uspto-grants-2015_08
Patent number
US09102684B2

Reaction notes

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