Sodium → 1-[4-chloro-6-[1-(1-ethoxyethyl)-1H-pyrazol-4-yl]-3',5'-difluoro-5-methylbiphenyl-2-yl]ethanone

HRID 510894Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 510894
[Na].Br[C:3]1[C:8]([C:9]2[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([F:16])[CH:10]=2)=[C:7]([C:17](=[O:19])[CH3:18])[CH:6]=[C:5]([Cl:20])[C:4]=1[CH3:21].[CH2:22]([O:24][CH:25]([N:27]1[CH:31]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:29]=[N:28]1)[CH3:26])[CH3:23]>O.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:20][C:5]1[C:4]([CH3:21])=[C:3]([C:30]2[CH:29]=[N:28][N:27]([CH:25]([O:24][CH2:22][CH3:23])[CH3:26])[CH:31]=2)[C:8]([C:9]2[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([F:16])[CH:10]=2)=[C:7]([C:17](=[O:19])[CH3:18])[CH:6]=1

Komponenten

7

Edukt 3

HCID 5360545SodiumHCID 467367981-(1-Ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 866668111-(6-Bromo-4-chloro-3',5'-difluoro-5-methylbiphenyl-2-yl)ethanone

Produkt 1

HCID 866668151-[4-chloro-6-[1-(1-ethoxyethyl)-1H-pyrazol-4-yl]-3',5'-difluoro-5-methylbiphenyl-2-yl]ethanoneAusbeute 40,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of sodium hydrogenecarbonate (0.093 g, 1.1 mmol) in water (2 mL) was added a solution of 1-(6-bromo-4-chloro-3′,5′-difluoro-5-methylbiphenyl-2-yl)ethanone (0.20 g, 0.56 mmol) in toluene (2 mL) followed by 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.18 g, 0.67 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.064 g, 0.056 mmol). The mixture was bubbled with N2 for 5 min and then heated at 90° C. overnight. The organic layer was concentrated and flashed on silica gel (eluting with 0-20% of ethyl acetate in hexanes) to afford the desired product (94 mg, 40%). LCMS calculated for C22H22ClF2N2O2 (M+H)+: m/z=419.1. found: 419.1.

Aufarbeitung

  1. customThe mixture was bubbled with N2 for 5 min
  2. concentrationThe organic layer was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-6e11e7954d0844fea855a1792f89f497
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096600B2

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