4-Fluorobenzyl bromide → ethyl 2-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylate

HRID 554904

Reaktionsgleichung

Reaktionsgleichung von HRID 554904
BrCC1CC1(F)F.Br[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1.[CH3:17][C:18]1[N:19]=[C:20]([N:28]2[C:32](=[O:33])[NH:31][N:30]=[CH:29]2)[S:21][C:22]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24]>>[F:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][N:31]2[C:32](=[O:33])[N:28]([C:20]3[S:21][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:18]([CH3:17])[N:19]=3)[CH:29]=[N:30]2)=[CH:11][CH:12]=1

Komponenten

4

Edukt 3

HCID 680214-Fluorobenzyl bromideHCID 27614022-(Bromomethyl)-1,1-difluorocyclopropaneHCID 57920013ethyl 4-methyl-2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylate

Produkt 1

HCID 57919964ethyl 2-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylateAusbeute 84 %

Versuchsvorschrift

Following the procedure as described in Preparation 13, making variation as required to replace bromomethyl-2,2-difluorocyclopropane with 1-(bromomethyl)-4-fluorobenzene to react with ethyl 4-methyl-2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylate in place of ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate, the title compound was obtained as a white solid in 84% yield: 1H NMR (300 MHz, CDCl3) δ 8.27 (s, 1H), 7.47-7.30 (m, 2H), 7.11-6.97 (m, 2H), 4.98 (s, 2H), 4.32 (q, J=7.1 Hz, 2H), 2.65 (s, 3H), 1.34 (t, J=7.1 Hz, 3H); MS (ES+) m/z 363.1 (M+1).

Aufarbeitung

  1. customas described in Preparation 13

Quellen und Nachweise

ORD-Eintrag
ord-c271ab341e6042b38182d1ef200c9b91
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08049016B2

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