Water → (6-Chloro-4-pyrrolidin-1-yl-pyridin-2-yl)-(4-trifluoromethoxy-phenyl)-amine

HRID 1437747Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1437747
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[C:4]([Cl:13])[N:3]=1.CC(C)([O-])C.[K+].[F:20][C:21]([F:31])([F:30])[O:22][C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1.O>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[Cl:13][C:4]1[N:3]=[C:2]([NH:29][C:26]2[CH:27]=[CH:28][C:23]([O:22][C:21]([F:20])([F:30])[F:31])=[CH:24][CH:25]=2)[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 6008484-(Trifluoromethoxy)anilineHCID 116442082,6-Dichloro-4-pyrrolidino-pyridineHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 11667597(6-Chloro-4-pyrrolidin-1-yl-pyridin-2-yl)-(4-trifluoromethoxy-phenyl)-amineAusbeute 44,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 634876Binap, (A+-)-KatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 2,6-dichloro-4-pyrrolidino-pyridine (1.0 g, 4.62 mmol) in toluene (6 mL) were added potassium tert-butoxide (0.1556 g, 1.38 mmol), palladium(II)acetate (26 mg, 0.115 mmol), BINAP (36 mg, 0.057 mmol) and 4-trifluoromethoxyphenylamine (246 mg, 1.38 mmol), in a 10 mL reaction vessel. This reaction mixture was subjected the microwave radiation, in which the microwave power was 250 W, to attain a reaction temperature of 150° C. After this reaction proceeded for 30 min, water (200 mL) was added to the reaction mixture and the reaction product was extracted with ethyl acetate. The organic layer was dried over sodium sulphate, filtered, and the filtrate concentrated under vacuum. The product was purified through column chromatography using 230-400 mesh silica gel to afford the desired compound as light brown solid (220 mg, yield 14%).

Aufarbeitung

  1. customin a 10 mL reaction vessel
  2. customa reaction temperature of 150° C
  3. extractionthe reaction product was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum
  7. customThe product was purified through column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3ab105d1ad284f9c9c13da1050176bd1
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07622486B2

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