Hydrochloric Acid → Ethyl 4-(4-bromo-2-fluoroanilino)-6-chloronicotinate

HRID 917749

Reaktionsgleichung

Reaktionsgleichung von HRID 917749
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.Cl[C:11]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][N:14]=[C:13]([Cl:22])[CH:12]=1.Cl>CCO>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:11]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][N:14]=[C:13]([Cl:22])[CH:12]=2)=[C:4]([F:9])[CH:3]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 1230504-Bromo-2-fluoroanilineHCID 600045Ethyl 4,6-dichloropyridine-3-carboxylate

Produkt 1

HCID 23630707Ethyl 4-(4-bromo-2-fluoroanilino)-6-chloronicotinateAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

4-Bromo-2-fluoroaniline and ethyl 4,6-dichloronicotinate were reacted in a mixture of EtOH and conc. HCl as for example 33, step A. The resultant solid was isolated by filtration and washed with 10% Et2O/Hexane, to give ethyl 4-(4-bromo-2-fluoroanilino)-6-chloronicotinate (58%); m.p. (EtOH/water) 150-152° C. 1H NMR [400 MHz, CDCl3] δ 9.74 (br s, 1H), 8.81 (s, 1H), 7.41 (dd, J=9.6, 2.2 Hz, 1H), 7.38-7.35 (m, 1H), 7.25 (t, J=8.3 Hz, 1H), 6.71 (d, J=1.5 Hz, 1H), 4.42 (q, J=7.1 Hz, 2H), 1.43 (t, J=7.1 Hz, 3H). MS (FAB+) 375 (16%).

Aufarbeitung

  1. customThe resultant solid was isolated by filtration
  2. washwashed with 10% Et2O/Hexane

Quellen und Nachweise

ORD-Eintrag
ord-19cf6923cf75409b95e10d84dd79abf4
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273877B2

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