Cesium carbonate → HCID 53371804, Verbindung

HRID 2409235

Reaktionsgleichung

Cl[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=2[F:22])[CH:3]=1.[NH2:23][C:24]1[CH:29]=[CH:28][N:27]=[CH:26][N:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>O1CCOCC1.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]>[F:22][C:13]1[CH:14]=[CH:15][C:16]([C:18]([F:21])([F:20])[F:19])=[CH:17][C:12]=1[C:4]1[CH:3]=[C:2]([NH:23][C:24]2[CH:29]=[CH:28][N:27]=[CH:26][N:25]=2)[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Komponenten

Reaktionsbedingungen

Temperatur: 140 °C

Versuchsvorschrift

To a solution of 307 mg (0.94 mmol) 4-chloro-2-(2-fluoro-5-trifluoromethyl-phenyl)-[1,8]naphthyridine in 10 ml dioxane under nitrogen, 89 mg (0.94 mmol) 4-aminopyrimidine, 612 mg (1.88 mmol) cesium carbonate, 54 mg (0.093 mmol) 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene and 34 mg (0.038 mmol) tris(dibenzylideneaceton)-dipalladium(0) were added and heated in a microwave apparatus to 140° C. for 30 minutes. The reaction mixture was partitioned between dichloromethane and water. The organic phase was dried and the product chromatographed on a silica gel column with dichloro-methane/methanol. This yielded [2-(2-fluoro-5-trifluoromethyl-phenyl)-[1,8]naphthyridin-4-yl]-pyrimidin-4-yl-amine as beige crystals; HPLC-MS: 1.72 min, [M+H] 386.

Aufarbeitung

customThe reaction mixture was partitioned between dichloromethane and water
customThe organic phase was dried
customthe product chromatographed on a silica gel column with dichloro-methane/methanol
custom1.72 min, [M+H] 386

Quellen und Nachweise

ORD-Eintrag: ord-b8c01926ccf341a9a15747f641a5d473
Quelldatensatz: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08815893B2

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