Cesium carbonate → 1,3-dimethyl-N-{3-methyl-5-[(6-nitropyridin-3-yl)oxy]phenyl}-1H-pyrazole-5-carboxamide

HRID 1874344

Reaktionsgleichung

Reaktionsgleichung von HRID 1874344
[OH:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[N:16]([CH3:17])[N:15]=[C:14]([CH3:18])[CH:13]=2)=[O:11])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:26]1[CH:27]=[CH:28][C:29]([N+:32]([O-:34])=[O:33])=[N:30][CH:31]=1>CN(C)C=O>[CH3:17][N:16]1[C:12]([C:10]([NH:9][C:4]2[CH:3]=[C:2]([O:1][C:26]3[CH:31]=[N:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=3)[CH:7]=[C:6]([CH3:8])[CH:5]=2)=[O:11])=[CH:13][C:14]([CH3:18])=[N:15]1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 8176205-Bromo-2-nitropyridineHCID 57749292N-(3-hydroxy-5-methylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide

Produkt 1

HCID 577491751,3-dimethyl-N-{3-methyl-5-[(6-nitropyridin-3-yl)oxy]phenyl}-1H-pyrazole-5-carboxamideAusbeute 64,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In the same manner as in Reference Example 12 and using N-(3-hydroxy-5-methylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide (8.30 g, 33.8 mmol), cesium carbonate (16.5 g, 50.8 mmol), 5-bromo-2-nitropyridine (6.54 g, 32.2 mmol) and N,N-dimethylformamide (40 mL) as starting materials, the title compound (7.68 g, 54%) was obtained as a pale-yellow oil.

Quellen und Nachweise

ORD-Eintrag
ord-7a86d82a52434fb09ba1eb6f80bafa55
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304557B2

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