Potassium Acetate → 5-(5,7-Difluoro-3-methyl-2-(4-methylpyridin-2-yl)quinolin-4-ylamino)pyridin-3-ylboronic acid

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Reaktionsgleichung

Br[C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([F:20])=[CH:16][C:17]=3[F:19])[N:12]=[C:11]([C:21]3[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][N:22]=3)[C:10]=2[CH3:28])[CH:5]=[N:6][CH:7]=1.[B:29]1(B2OC(C)(C)C(C)(C)O2)[O:33]C(C)(C)C(C)(C)[O:30]1.C([O-])(=O)C.[K+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.O1CCOCC1>[F:19][C:17]1[CH:16]=[C:15]([F:20])[CH:14]=[C:13]2[C:18]=1[C:9]([NH:8][C:4]1[CH:3]=[C:2]([B:29]([OH:33])[OH:30])[CH:7]=[N:6][CH:5]=1)=[C:10]([CH3:28])[C:11]([C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][N:22]=1)=[N:12]2

Komponenten

Reaktionsbedingungen

Temperatur: 95 °C

Versuchsvorschrift

A screwcap vial was charged with N-(5-bromopyridin-3-yl)-5,7-difluoro-3-methyl-2-(4-methylpyridin-2-yl)quinolin-4-amine (225 mg, 0.510 mmol), bis(pinacolato)diboron (194 mg, 0.77 mmol), bis(triphenylphosphine)palladium (II) chloride (35.8 mg, 0.051 mmol), potassium acetate (100 mg, 1.02 mmol), and 1,4-dioxane (5 mL). The mixture was stirred at 95° C. under nitrogen for 18 h, and cooled to rt. The desired product was extracted with DCM and EtOAc, and the combined organic layer was dried over magnesium sulfate and cond. This afforded crude 5-(5,7-difluoro-3-methyl-2-(4-methylpyridin-2-yl)quinolin-4-ylamino)pyridin-3-ylboronic acid. Mass Spectrum (ESI) m/e=407.1 (M+1).

Aufarbeitung

temperaturecooled to rt
extractionThe desired product was extracted with DCM and EtOAc
dry with materialthe combined organic layer was dried over magnesium sulfate and cond

Quellen und Nachweise

ORD-Eintrag: ord-489343e745da4ddabb462c48739abe40
Quelldatensatz: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08940724B2

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