2-Chloro-5-hydroxybenzeneboronic acid → 2'-Chloro-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-5'-hydroxy-biphenyl-2-carboxylic acid

HRID 1519348Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1519348
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=3)[N:14]=2)[CH:7]=[CH:6][C:5]=1Br.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][C:27]=1B(O)O>>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][C:27]=1[C:5]1[C:4]([C:3]([OH:2])=[O:24])=[CH:9][C:8]([C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=3)[N:14]=2)=[CH:7][CH:6]=1

Komponenten

3

Edukt 2

HCID 441193422-Chloro-5-hydroxybenzeneboronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Produkt 1

HCID 866798482'-Chloro-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-5'-hydroxy-biphenyl-2-carboxylic acidAusbeute 74,5 %

Versuchsvorschrift

Using the conditions of General Procedure B for Suzuki Coupling and Hydrolysis in Parallel Mode, 2-bromo-5-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-benzoic acid methyl ester (which may be prepared as described for Intermediate 6; 89 mg, 0.2 mmol) was reacted with and 2-chloro-5-hydroxybenzeneboronic acid (available from Combi-Blocks Inc.; 69 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 2′-chloro-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-5′-hydroxy-biphenyl-2-carboxylic acid (71 mg, 74%). 1H NMR (400 MHz, DMSO-d6) δ 13.01 (br s, 1H), 9.76 (s, 1H), 8.48 (s, 2H), 8.34 (d, J=2.0 Hz, 1H), 8.25 (dd, J=8.0, 1.8 Hz, 1H), 8.09 (dd, J=8.3, 2.0 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.43 (d, J=8.0 Hz, 1H), 7.27 (d, J=8.5 Hz, 1H), 6.78 (dd, J=8.7, 2.9 Hz, 1H), 6.71 (d, J=2.8 Hz, 1H).

Aufarbeitung

  1. customthe acid was purified

Quellen und Nachweise

ORD-Eintrag
ord-2067e8e0312c4c8380ba40ed091790fb
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073881B2

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