Cesium carbonate → 2-chloro-4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-6-methylpyridine

HRID 1498792

Reaktionsgleichung

[Cl:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.[CH3:10][C:11]1[N:15]=[C:14]([CH3:16])[NH:13][N:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([N:12]2[C:11]([CH3:10])=[N:15][C:14]([CH3:16])=[N:13]2)[CH:5]=[C:4]([CH3:9])[N:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A mixture of 2,4-dichloro-6-methylpyridine (24-1, 2.15 g, 13.3 mmol), 3,5-dimethyl-1H-1,2,4-triazole (1.29 g, 13.3 mmol), and cesium carbonate (5.20 g, 16.0 mmol) in DMF (15 mL) was heated at 100° C. for 20 hours and cooled to room temperature. The mixture was diluted with ethyl acetate (250 mL) and washed with brine (4×250 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel column chromatography (0-90% ethyl acetate in hexanes) to afford 2-chloro-4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-6-methylpyridine (24-2) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.34 (m, 1H), 7.29 (m, 1H), 2.64 (s, 3H), 2.62 (s, 3H), 2.41 (s, 3H). LRMS m/z (M+H) 223 found, 223 required. The regioisomer (24-3) was also obtained as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.71 (m, 1H), 7.10 (m, 1H), 2.83 (s, 3H), 2.54 (s, 3H), 2.41 (s, 3H). LRMS m/z (M+H) 223 found, 223 required.

Aufarbeitung

temperaturecooled to room temperature
washwashed with brine (4×250 mL)
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (0-90% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-458b33fc237b44f6be88f66762ef4c3e
Quelldatensatz: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09200001B2

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