2,3,4,5-Tetrafluoronitrobenzene → 5-cyclopropyl-N-(2,3,4-trifluoro-6-nitrophenyl)-1H-pyrazol-3-amine

HRID 1092253

Reaktionsgleichung

Reaktionsgleichung von HRID 1092253
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5](F)=[C:4]([F:12])[C:3]=1[F:13].CCN(C(C)C)C(C)C.[CH:23]1([C:26]2[NH:30][N:29]=[C:28]([NH2:31])[CH:27]=2)[CH2:25][CH2:24]1>C1COCC1>[CH:23]1([C:26]2[NH:30][N:29]=[C:28]([NH:31][C:5]3[C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]([F:1])=[C:3]([F:13])[C:4]=3[F:12])[CH:27]=2)[CH2:25][CH2:24]1

Komponenten

5

Edukt 3

HCID 796912,3,4,5-TetrafluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 27580143-cyclopropyl-1H-pyrazol-5-amine

Produkt 1

HCID 860798025-cyclopropyl-N-(2,3,4-trifluoro-6-nitrophenyl)-1H-pyrazol-3-amineAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To 1,2,3,4-tetrafluoro-5-nitrobenzene (3.0 g, 15.4 mmol) and DIEA (3.7 ml, 21.0 mmol) in dry THF (20 ml) was added 5-cyclopropyl-1H-pyrazol-3-amine (1.7 g, 14.0 mmol) in THF (5 ml) drop wise at 0° C. After addition, the reaction mixture was stirred at 25° C. for 16 hours. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane-EtOAc=4:1). This was recrystallized from Et2O (20 ml) and hexanes (˜150 ml) to give the title compound as red crystals (0.650 g, 16%). 1H NMR (400 MHz) 11.84 (s, 1H), 8.67 (s, 1H), 8.06 (m, 1H), 5.57 (s, 1H), 1.82 (m, 1H), 0.89 (m, 2H), 0.65 (m, 2H). MS: Calcd.: 298; Found: [M+H]+ 299.

Aufarbeitung

  1. additionAfter addition
  2. customThe solvent was removed under reduced pressure
  3. customthe resulted residue was purified by column chromatography (hexane-EtOAc=4:1)
  4. customThis was recrystallized from Et2O (20 ml) and hexanes (˜150 ml)

Quellen und Nachweise

ORD-Eintrag
ord-1eb80a444fff4110ae29f0834f9a65b6
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129403B2

Verknüpfte Notizen

Wird geladen…