Cesium fluoride → 4'-(tert-Butyl-methyl-sulfamoyl)-biphenyl-4-carboxylic acid methyl ester

HRID 1677136Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1677136
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:17][O:18][C:19](=[O:35])[C:20]1[CH:25]=[CH:24][C:23](B2OC(C)(C)C(C)(C)O2)=[CH:22][CH:21]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[F-].[Cs+]>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:17][O:18][C:19]([C:20]1[CH:25]=[CH:24][C:23]([C:2]2[CH:7]=[CH:6][C:5]([S:8](=[O:10])(=[O:9])[N:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:12])=[CH:4][CH:3]=2)=[CH:22][CH:21]=1)=[O:35]

Komponenten

6

Edukt 4

HCID 25953Cesium fluorideHCID 75806TricyclohexylphosphineHCID 2773500Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateHCID 57980036HCID 57980036, Verbindung

Produkt 1

HCID 579801654'-(tert-Butyl-methyl-sulfamoyl)-biphenyl-4-carboxylic acid methyl esterAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 167845palladium(II) acetateKatalysator

Versuchsvorschrift

Procedure S′: 4′-(tert-Butyl-methyl-sulfamoyl)-biphenyl-4-carboxylic acid methyl ester is prepared in a manner substantially analogous to Procedure O′ using 4-bromo-N-tert-butyl-N-methyl-benzenesulfonamide (459 mg, 1.5 mmol), 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (CAS 17136-80-0) (490 mg, 1.87 mmol), tricyclohexylphosphine (65 mg, 0.23 mmol), Pd(OAc)2 (34 mg, 0.15 mmol), and CsF (906 mg, 6 mmol) to give the intermediate 4′-(tert-Butyl-methyl-sulfamoyl)-biphenyl-4-carboxylic acid methyl ester (350 mg, 65% yield). MS (ES+) 384.1 (M+Na)+

Aufarbeitung

  1. customProcedure S′: 4′-(tert-Butyl-methyl-sulfamoyl)-biphenyl-4-carboxylic acid methyl ester is prepared in a manner substantially analogous to Procedure O′

Quellen und Nachweise

ORD-Eintrag
ord-d6fadad6ec084e9380e6d53fdfdeef55
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008301B2

Notizen zur Reaktion

Wird geladen…