Potassium Phosphate, Tribasic → 4-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-fluoro-benzoic acid methyl ester

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Reaktionsgleichung

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][CH3:9])[C:3]=1[C:10]#[C:11][C:12]1[CH:13]=[CH:14][C:15]([NH2:18])=[N:16][CH:17]=1.[F:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][C:25]=1[C:26]([O:28][CH3:29])=[O:27].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[Li+].[Cl-].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:29][O:28][C:26](=[O:27])[C:25]1[CH:24]=[CH:23][C:22]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][CH3:9])[C:3]=2[C:10]#[C:11][C:12]2[CH:17]=[N:16][C:15]([NH2:18])=[CH:14][CH:13]=2)=[CH:21][C:20]=1[F:19]

Komponenten

Reaktionsbedingungen

Temperatur: 95 °C

Versuchsvorschrift

The title compound is synthesized according to general procedure GP3 starting from 3.2 g (12.3 mmol) 5-(4-Chloro-2-ethyl-pyridin-3-ylethynyl)-pyridin-2-ylamine (A-30) using 3.6 g (18.4 mmol) 3-Fluoro-4-methoxycarbonylphenyl boronic acid, 561 mg (0.61 mmol) Pd2(dba)3, 877 mg (1.84 mmol) X-Phos, 519 mg (12.3 mmol) LiCl and 3.39 g (14.7 mmol) K3PO4 in a mixture of 60 mL 1,2-dimethoxyethane and 10 mL water. The reaction mixture is stirred for 16 h at 95° C. After completion of the reaction, the mixture is poured into water and the formed precipitate is collected by filtration. The product is purified by chromatography on silica gel using an DCM/MeOH-mixture (3% MeOH, flow 55 mL/min). Yield: 2.46 g (53%).

Aufarbeitung

customAfter completion of the reaction
filtrationthe formed precipitate is collected by filtration
customThe product is purified by chromatography on silica gel using an DCM/MeOH-mixture (3% MeOH, flow 55 mL/min)

Quellen und Nachweise

ORD-Eintrag: ord-c5567166cb384475b823f68fc3780a42
Quelldatensatz: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09090564B2

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