Sodium Sulfide → HCID 67253153, compound

HRID 2167184Notes

Reaction equation

HRID 2167184 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([C@@H:12]([C:18]1[CH:23]=[CH:22][C:21]([O:24]C)=[C:20]([O:26][CH2:27][CH3:28])[CH:19]=1)[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:7]2.[Si](I)(C)(C)C.[S-2].[Na+].[Na+]>>[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([C@@H:12]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([O:26][CH2:27][CH3:28])[CH:19]=1)[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:7]2

Participants

4

Reactant 3

HCID 14804Sodium SulfideHCID 85247Trimethylsilyl iodideHCID 66718531(S)-7-amino-2-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)isoindolin-1-one

Product 1

HCID 67253153HCID 67253153, compoundYield 62.2%

Conditions

Temperature
80 °C

Procedure

A mixture of (S)-7-amino-2-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)isoindolin-1-one (10 g, 24.7 mmol) and TMSI (50 g, 250 mmol) was heated to 80° C. for 2 hours. The mixture was cooled to 0° C. in an ice-water bath. To the mixture, was added 5% aqueous sodium sulfide solution. The mixture was stirred at room temperature until all solid dissolved. The mixture was extracted with methylene chloride. The organic layer was washed with brine. The solvent was removed in vacuo to give a foam. The crude mixture was purified by column chromatography (silica gel. MeOH/CH2Cl2) to give (S)-7-amino-2-(1-(3-ethoxy-4-hydroxyphenyl)-2-(methylsulfonyl)ethyl)isoindolin-1-one (6 g), which was used in the next step without further purification.

Workup

  1. temperatureThe mixture was cooled to 0° C. in an ice-water bath
  2. dissolutiondissolved
  3. extractionThe mixture was extracted with methylene chloride
  4. washThe organic layer was washed with brine
  5. customThe solvent was removed in vacuo
  6. customto give a foam
  7. customThe crude mixture was purified by column chromatography (silica gel. MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-8d81374a26394b0a854b510a9687d06a
Source dataset
uspto-grants-2015_06
Patent number
US09045417B2

Reaction notes

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