Cesium fluoride → benzyl 4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)benzylcarbamate

HRID 573814

Reaktionsgleichung

Reaktionsgleichung von HRID 573814
Br[C:2]1[N:6]=[CH:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[N:3]=1.CC1(C)C(C)(C)OB([C:25]2[CH:42]=[CH:41][C:28]([CH2:29][NH:30][C:31](=[O:40])[O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[CH:27][CH:26]=2)O1.F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[F-].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:14][C:13]([F:16])([F:15])[C:10]1[CH:11]=[CH:12][C:7]([N:4]2[CH:5]=[N:6][C:2]([C:25]3[CH:42]=[CH:41][C:28]([CH2:29][NH:30][C:31](=[O:40])[O:32][CH2:33][C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)=[CH:27][CH:26]=3)=[N:3]2)=[CH:8][CH:9]=1

Komponenten

6

Edukt 4

HCID 25953Cesium fluorideHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 904043003-bromo-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazoleHCID 90404705benzyl N-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}carbamate

Produkt 1

HCID 90403882benzyl 4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)benzylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 167845palladium(II) acetateKatalysator

Versuchsvorschrift

The title compound was prepared as described in Example 10 using 3-bromo-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazole (C1b), benzyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylcarbamate (C13), tri-tert-butylphosphonium tetrafluoroborate, palladium(II) acetate, and cesium fluoride and isolated as a white solid (0.846 g, 36%): 1H NMR (400 MHz, DMSO-d6) δ 9.53 (s, 1H), 8.28-8.14 (m, 2H), 8.16-8.04 (m, 2H), 8.04-7.95 (m, 2H), 7.92 (t, J=6.2 Hz, 1H), 7.49-7.13 (m, 7H), 5.07 (s, 2H), 4.29 (d, J=6.2 Hz, 2H); 19F NMR (376 MHz, DMSO-d6) δ −60.79; ESIMS m/z 453 ([M+H]+).

Quellen und Nachweise

ORD-Eintrag
ord-d9d417e1172045bab6b96d347f04bf64
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029560B2

Verknüpfte Notizen

Wird geladen…