2,3,4-Trifluorobenzoic acid → 2-(4-Butyl-2-fluoroanilino)-3,4-difluorobenzoic acid

HRID 1793048Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1793048
F[C:2]1[C:10]([F:11])=[C:9]([F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:13]([C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[C:19]([F:24])[CH:18]=1)[CH2:14][CH2:15][CH3:16].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[CH2:13]([C:17]1[CH:23]=[CH:22][C:20]([NH:21][C:2]2[C:10]([F:11])=[C:9]([F:12])[CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])=[C:19]([F:24])[CH:18]=1)[CH2:14][CH2:15][CH3:16]

Komponenten

5

Edukt 3

HCID 3029322,3,4-Trifluorobenzoic acidHCID 2733832Lithium HexamethyldisilazideHCID 220256384-Butyl-2-fluoroaniline

Produkt 1

HCID 220256902-(4-Butyl-2-fluoroanilino)-3,4-difluorobenzoic acidAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2,3,4-Trifluorobenzoic acid and 4-butyl-2-fluoroaniline were reacted in the presence of LiHMDS solution in THF by the general procedure of Example 1, Step B, affording crude 2-(4-butyl-2-fluoroanilino)-3,4-difluorobenzoic acid after workup. The crude material was further purified by flash chromatography on silica (10% EtOAc/Hexane as eluant) to give the desired compound (40%). 1H NMR [400 MHz, CH30D] δ 7.86 (ddd, J=8.4, 5.8, 2.1 Hz, 1 H), 6.96–6.86 (m, 3 H), 6.78 (ddd, J=9.4, 9.4, 7.1 Hz, 1 H), 2.58 (t, J=7.7 Hz, 2 H), 1.63–1.55 (m, 2 H), 1.36 (sextet, J=7.4, 2H), 0.94 (t, J=7.5, 3 H). LCMS (ACPI+) 329 (100%).

Aufarbeitung

  1. customaffording crude 2-(4-butyl-2-fluoroanilino)-3,4-difluorobenzoic acid after workup
  2. customThe crude material was further purified by flash chromatography on silica (10% EtOAc/Hexane as eluant)

Quellen und Nachweise

ORD-Eintrag
ord-b6599587cad34dc3995cc971754ba0f6
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07078438B2

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