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

HRID 2053256Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2053256
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-759d15183ff7421ea59b1523460e808e
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07326732B2

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