Pyridine → 2,3,4,5,6-Pentafluorophenyl 4-(4-bromo-2-fluoroanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate

HRID 917753Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 917753
[Br:1][C:2]1[CH:19]=[CH:18][C:5]([NH:6][C:7]2[C:8]([C:15]([OH:17])=[O:16])=[CH:9][N:10]([CH3:14])[C:11](=[O:13])[CH:12]=2)=[C:4]([F:20])[CH:3]=1.FC(F)(F)C(O[C:26]1[C:31]([F:32])=[C:30]([F:33])[C:29]([F:34])=[C:28]([F:35])[C:27]=1[F:36])=O.N1C=CC=CC=1>C1COCC1>[Br:1][C:2]1[CH:19]=[CH:18][C:5]([NH:6][C:7]2[C:8]([C:15]([O:17][C:26]3[C:27]([F:36])=[C:28]([F:35])[C:29]([F:34])=[C:30]([F:33])[C:31]=3[F:32])=[O:16])=[CH:9][N:10]([CH3:14])[C:11](=[O:13])[CH:12]=2)=[C:4]([F:20])[CH:3]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 115809254-(4-Bromo-2-fluorophenylamino)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid

Produkt 1

HCID 589628492,3,4,5,6-Pentafluorophenyl 4-(4-bromo-2-fluoroanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-(4-Bromo-2-fluoroanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid and pentafluorophenyl trifluoroacetate were reacted in the presence of pyridine in THF as for example 4, step A. The crude residue was purified by flash chromatography on silica gel (60% EtOAc/Hexane) to give 2,3,4,5,6-pentafluorophenyl 4-(4-bromo-2-fluoroanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate (97%). 1H NMR [400 MHz, (CD3)2SO] δ 9.03 (s, 1H), 8.70 (s, 1H), 7.71 (dd, J=10.6, 2.0 Hz, 1H), 7.49 (dd, J=8.5, 2.0 Hz, 1H), 7.46 (t, J=8.7 Hz, 1H), 5.34 (d, J=1.6 Hz, 1H), 3.49 (s, 3H).

Aufarbeitung

  1. customThe crude residue was purified by flash chromatography on silica gel (60% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e6bb761702a74ddd9f639b912a740ddb
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273877B2

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