Water → (S)-Methyl 2-(6-(5-aminopyridin-2-yl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

HRID 403984Notes

Reaction equation

HRID 403984 reaction equation
[CH3:1][CH:2]([CH3:27])[C@H:3]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][N:18]=3)=[CH:13][CH:14]=2)[C:9]1=[O:26])[C:4]([O:6][CH3:7])=[O:5].[Cl-].[NH4+].O>CCO.C(OCC)(=O)C.[Fe]>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([C:12]2[CH:11]=[C:10]3[C:15]([CH2:16][N:8]([C@@H:3]([CH:2]([CH3:27])[CH3:1])[C:4]([O:6][CH3:7])=[O:5])[C:9]3=[O:26])=[CH:14][CH:13]=2)=[N:18][CH:19]=1

Participants

7

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 131731547(S)-Methyl 3-methyl-2-(6-(5-nitropyridin-2-yl)-1-oxoisoindolin-2-yl)butanoate

Product 1

HCID 131731548(S)-Methyl 2-(6-(5-aminopyridin-2-yl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound of example 391 (1.5 g, 0.0040 mol), iron (0.533 g, 0.0095 mol) and ammonium chloride (0.930 g, 0.0174 mol) in EtOH: H2O (22.5 mL, 15:7.5) was refluxed for about 16 h. After completion of the reaction, the reaction mixture was filtered through celite. The filtrate was concentrated to obtain a residue which was dissolved in ethyl acetate and washed with water and brine, dried over anhydrous sodium sulfate and concentrated to obtain a residue, which was purified by column chromatography (silica gel, 30% ethyl acetate in petroleum ether) to obtain the title compound.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered through celite
  3. concentrationThe filtrate was concentrated
  4. customto obtain a residue which
  5. washwashed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customto obtain a residue, which
  9. customwas purified by column chromatography (silica gel, 30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-c110c924b0f84eeb8147f4f51a4930f3
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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