(3-Chlorophenyl)boronic acid → {3-[(3'-Chloro-4-fluoro-biphenyl-3-carbonyl)-amino]-phenoxy}-acetic acid

HRID 1717134Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1717134
C([O:3][C:4](=[O:24])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14](=[O:23])[C:15]2[CH:20]=[C:19](Br)[CH:18]=[CH:17][C:16]=2[F:22])[CH:8]=1)C.[Cl:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1>>[Cl:25][C:26]1[CH:31]=[C:30]([C:19]2[CH:18]=[CH:17][C:16]([F:22])=[C:15]([C:14]([NH:13][C:9]3[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=3)[O:6][CH2:5][C:4]([OH:3])=[O:24])=[O:23])[CH:20]=2)[CH:29]=[CH:28][CH:27]=1

Komponenten

3

Edukt 2

HCID 2734323(3-Chlorophenyl)boronic acidHCID 40356283[3-(5-Bromo-2-fluoro-benzoylamino)-phenoxy]-acetic acid ethyl ester

Produkt 1

HCID 59654666{3-[(3'-Chloro-4-fluoro-biphenyl-3-carbonyl)-amino]-phenoxy}-acetic acid

Versuchsvorschrift

The phenyl bromide (139) (50 mg, 0.13 mmol) was coupled to 3-chloro-phenylboronic acid (20 mg, 0.13 mmol) using Method E. During this reaction, hydrolysis occurred and the residue was extracted using Work-up E1. The crude product was then triturated with TBME (2 ml), DCM (2 ml), and recrystallised from a hot 10% EtOH in H2O mixture to give the title compound.

Aufarbeitung

  1. customDuring this reaction, hydrolysis
  2. extractionthe residue was extracted
  3. customThe crude product was then triturated with TBME (2 ml), DCM (2 ml)
  4. customrecrystallised from a hot 10% EtOH in H2O mixture

Quellen und Nachweise

ORD-Eintrag
ord-9f28926e9c204dc6aef4eb6c0da4a8e0
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803841B2

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