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Potassium Phosphate, Tribasic → (2-(4-Chloro-phenyl)-2-[4-(1H-pyrazol-4-yl)-phenyl]-ethyl)-methyl-amine

HRID 1798366
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1798366
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:9][NH:10][CH3:11])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:27]2[CH:28]=[N:29][NH:30][CH:31]=2)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(O)C.CO.C1(C)C=CC=CC=1.O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([C:27]3[CH:28]=[N:29][NH:30][CH:31]=3)=[CH:3][CH:4]=2)[CH2:9][NH:10][CH3:11])=[CH:13][CH:14]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 57691393[2-(4-Bromo-phenyl)-2-(4-chloro-phenyl)ethyl]-methyl-amine

Produkt 1

HCID 11438353(2-(4-Chloro-phenyl)-2-[4-(1H-pyrazol-4-yl)-phenyl]-ethyl)-methyl-amineAusbeute 84,2 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 178418851
HCID 178418851, Verbindung
Katalysator
HCID 702EthanolLösungsmittel
HCID 887MethanolLösungsmittel
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of [2-(4-Bromo-phenyl)-2-(4-chloro-phenyl)-ethyl]-methyl-amine (6.1 g, 13.716 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (5.3 g, 27.431 mmol) and K3PO4 (10.19 g, 48.00 mmol) in ethanol (7.5 ml), methanol (11.5 ml), toluene (7.5 ml) and water (11.5 ml) was purged with nitrogen for 2 minutes. Bis(tri-t-butylphosphine)palladium (0) (175 mg, 2.5 mol %) was then added and the reaction mixture purged with nitrogen for a further 2 minutes. The mixture was then heated to 80° C., under nitrogen for a period of 17 hours. The solvents were removed and the residue was partitioned between ethyl acetate and 2N NaOH. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The crude reaction mixture was purified by column chromatography (SiO2), eluting with dichloromethane: methanol: acetic acid:water (90:18:3:2) to afford the title compound (3.6 g); LCMS (PS-A2) Rt 2.08 min [M+H]+ 312.

Aufarbeitung

  1. customthe reaction mixture purged with nitrogen for a further 2 minutes
  2. customThe solvents were removed
  3. customthe residue was partitioned between ethyl acetate and 2N NaOH
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe crude reaction mixture
  9. customwas purified by column chromatography (SiO2)
  10. washeluting with dichloromethane: methanol: acetic acid:water (90:18:3:2)

Quellen und Nachweise

ORD-Eintrag
ord-b0a726fbb4cd422db7f33c27beaccbf9
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08343953B2

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