Aniline → 4-[4-(6-Fluoro-1-oxo-1,3-dihydro-isoindol-2-yl)-phenyl]-butyric acid ethyl ester

HRID 1023698Notes

Reaction equation

HRID 1023698 reaction equation
C(O[C:4](=[O:14])[C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=1[CH2:12]Br)C.[CH2:15]([O:17][C:18](=[O:29])[CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=1)[CH3:16].NC1C=CC=CC=1>>[CH2:15]([O:17][C:18](=[O:29])[CH2:19][CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([N:28]2[CH2:12][C:6]3[C:5](=[CH:10][C:9]([F:11])=[CH:8][CH:7]=3)[C:4]2=[O:14])=[CH:26][CH:27]=1)[CH3:16]

Participants

4

Reactant 3

HCID 6115AnilineHCID 10013251Ethyl 4-(4-aminophenyl)butanoateHCID 14626277Ethyl 2-(bromomethyl)-5-fluorobenzoate

Product 1

HCID 670457314-[4-(6-Fluoro-1-oxo-1,3-dihydro-isoindol-2-yl)-phenyl]-butyric acid ethyl ester

Procedure

By using 2-bromomethyl-5-fluorobenzoic acid ethyl ester and 4-(4-amino-phenyl)butyric acid ethyl ester instead of 2-bromomethyl-6-nitro-benzoic acid methyl ester and aniline used in Example 25, synthesis was performed in the same manner as that of Example 25 to obtain 4-[4-(6-fluoro-1-oxo-1,3-dihydro-isoindol-2-yl)-phenyl]-butyric acid ethyl ester as an orange oily substance.

Workup

  1. customused in Example 25, synthesis

Sources & evidence

ORD record
ord-c3db96fe9c2b4812b787610d9d99e177
Source dataset
uspto-grants-2014_05
Patent number
US08722723B2

Reaction notes

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