(4-Fluoro-3-methylphenyl)boronic acid → 2-(3-(4-Fluoro-3-methyl-phenyl)-5-phenyl-(1,2,4)triazol-1-yl)-1-(4-pyrimidin-2-yl-piperazin-1-yl)-ethanone

HRID 336388

Reaktionsgleichung

Br[C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]([CH2:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[N:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[CH2:18][CH2:17]2)=[O:15])[N:3]=1.C(OC([O-])=O)([O-])=O.[Na+].[Na+].[F:37][C:38]1[CH:43]=[CH:42][C:41](B(O)O)=[CH:40][C:39]=1[CH3:47]>O1CCOCC1.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>[F:37][C:38]1[CH:43]=[CH:42][C:41]([C:2]2[N:6]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:4]([CH2:13][C:14]([N:16]3[CH2:21][CH2:20][N:19]([C:22]4[N:27]=[CH:26][CH:25]=[CH:24][N:23]=4)[CH2:18][CH2:17]3)=[O:15])[N:3]=2)=[CH:40][C:39]=1[CH3:47]

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

15 mg tetrakis(triphenylphosphine)palladium(0) was added to 100 mg 2-(3-bromo-5-phenyl-(1,2,4)triazol-1-yl)-1-(4-pyrimidin-2-yl-piperazin-1-yl)-ethanone, 500 μL 2 mol/L aqueous sodiumdicarbonate solution and 43 mg 4-fluoro-3-methylphenylboronic acid in 10 mL dioxane under nitrogen. The reaction was stirred over night at 120° C. The reaction was filltered and evaporated. The residue was purified by HPLC to give 32 mg of the desired product.

Aufarbeitung

customevaporated
customThe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag: ord-84aea2a5210d410c990142fca04841a1
Quelldatensatz: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08889677B2

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