3-(4-Difluoromethoxy-3-ethoxy-phenyl)-3-(7-nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester → 3-(7-Amino-1-oxo-1,3-dihydro-isoindol-2-yl)-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionic acid methyl ester

HRID 1367073Notes

Reaction equation

HRID 1367073 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH2:4][CH:5]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH:26]([F:28])[F:27])=[C:21]([O:29][CH2:30][CH3:31])[CH:20]=1)[N:6]1[CH2:14][C:13]2[C:8](=[C:9]([N+:15]([O-])=O)[CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:18]>[Pd]>[CH3:1][O:2][C:3](=[O:32])[CH2:4][CH:5]([N:6]1[CH2:14][C:13]2[C:8](=[C:9]([NH2:15])[CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:18])[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH:26]([F:28])[F:27])=[C:21]([O:29][CH2:30][CH3:31])[CH:20]=1

Participants

3

Reactant 1

HCID 100724433-(4-Difluoromethoxy-3-ethoxy-phenyl)-3-(7-nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester

Product 1

HCID 103648123-(7-Amino-1-oxo-1,3-dihydro-isoindol-2-yl)-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

3-(7-Amino-1-oxo-1,3-dihydro-isoindol-2-yl)-3-(4-difluoromethoxy-3-ethoxy-phenyl)-propionic acid methyl ester was prepared by the procedure of example 14 from 3-(4-difluoromethoxy-3-ethoxy-phenyl)-3-(7-nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester (9.1 g, 0.02 mol) and palladium on carbon under hydrogen pressure (50 psi). The product was used in the next step without further purification.

Workup

  1. customThe product was used in the next step without further purification

Sources & evidence

ORD record
ord-bbf9845c76bf4a27917aca0979e6c735
Source dataset
uspto-grants-2011_02
Patent number
US07893102B2

Reaction notes

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