Ethyl 2-(3-aminophenoxy)acetate → [3-(5-Bromo-2-fluoro-benzoylamino)-phenoxy]-acetic acid ethyl ester

HRID 1444351Notes

Reaction equation

HRID 1444351 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[CH2:12]([O:14][C:15](=[O:25])[CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[CH:19]=1)[CH3:13]>>[CH2:12]([O:14][C:15](=[O:25])[CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:7](=[O:9])[C:6]2[CH:10]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=2[F:11])[CH:19]=1)[CH3:13]

Participants

3

Reactant 2

HCID 412308Ethyl 2-(3-aminophenoxy)acetateHCID 27363155-Bromo-2-fluorobenzoic acid

Product 1

HCID 40356283[3-(5-Bromo-2-fluoro-benzoylamino)-phenoxy]-acetic acid ethyl ester

Procedure

5-Bromo-2-fluoro-benzoic acid (250 mg, 1.14 mmol) was coupled to aniline (64) (245 mg, 1.25 mmol) using Method D. The residue was purified by column chromatography eluting with a stepped gradient of 10-15% EtOAc in heptane to give the title compound.

Workup

  1. customThe residue was purified by column chromatography
  2. washeluting with a stepped gradient of 10-15% EtOAc in heptane

Sources & evidence

ORD record
ord-e3c279bba8bf4698a6ae01d108be464f
Source dataset
uspto-grants-2010_02
Patent number
US07662839B2

Reaction notes

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