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

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Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of sodium hydrogenecarbonate (0.049 g, 0.58 mmol) in water (1 mL) was added a solution of 1-(6-bromo-4-chloro-3′-fluoro-5-methylbiphenyl-2-yl)ethanone (0.10 g, 0.29 mmol) in toluene (1 mL) followed by 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.093 g, 0.35 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.017 g, 0.015 mmol). The resulting mixture was bubbled with N2 for 5 min and then heated at 80° C. over a weekend. The organic layer was concentrated and purified on silica gel (eluting with 0-30% of ethyl acetate in hexanes) to give the desired product (37 mg, 32%). LCMS calculated for C22H23ClFN2O2 (M+H)+: m/z=401.1. found: 401.1.

Aufarbeitung

customThe resulting mixture was bubbled with N2 for 5 min
concentrationThe organic layer was concentrated
custompurified on silica gel (eluting with 0-30% of ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-954c691785104c4a83f233f3f2761784
Quelldatensatz: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09096600B2

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