(S)-2-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-7-nitroisoindolin-1-one → (S)-7-amino-2-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)isoindolin-1-one

HRID 55933Notes

Reaction equation

HRID 55933 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C@H:12]([N:18]2[CH2:26][C:25]3[C:20](=[C:21]([N+:27]([O-])=O)[CH:22]=[CH:23][CH:24]=3)[C:19]2=[O:30])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]>C(OCC)(=O)C.[Pd]>[NH2:27][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:20]=1[C:19](=[O:30])[N:18]([C@@H:12]([C:6]1[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=1)[CH2:13][S:14]([CH3:17])(=[O:15])=[O:16])[CH2:26]2

Participants

4

Reactant 1

HCID 58224189(S)-2-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-7-nitroisoindolin-1-one

Product 1

HCID 66718531(S)-7-amino-2-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)isoindolin-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl 2-(bromomethyl)-6-nitrobenzoate and H—CH2-CH3-Compound D, triethyl amine in DMF is heated to reflux. The solvent is removed in vacuo. The crude mixture is purified by column chromatography to give (S)-2-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-7-nitroisoindolin-1-one. A mixture of (S)-2-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-7-nitroisoindolin-1-one and Pd/C in ethyl acetate is shaken under hydrogen. The suspension is filtered thru a pad of Celite. The solvent is removed in vacuo. The crude mixture is purified by column chromatography to give (S)-7-amino-2-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)isoindolin-1-one.

Workup

  1. filtrationThe suspension is filtered
  2. customThe solvent is removed in vacuo
  3. customThe crude mixture is purified by column chromatography

Sources & evidence

ORD record
ord-9a64da0da8fa47c79f5ef24c01cad2b5
Source dataset
uspto-grants-2016_09
Patent number
US09434689B2

Reaction notes

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