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Ammonium Chloride → HCID 86700075, Verbindung

HRID 1428122
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1428122
I[C:2]1[C:3]([NH2:10])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH3:9].CC1(C)C(C)(C)OB([C:19]2[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=2)O1.[F-].[Cs+].[Cl-].[NH4+]>CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[NH2:23][C:22]1[CH:24]=[CH:25][C:19]([C:2]2[C:3]([NH2:10])=[N:4][CH:5]=[CH:6][C:7]=2[O:8][CH3:9])=[CH:20][CH:21]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 25953Cesium fluorideHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 242292063-Iodo-4-methoxypyridin-2-amine

Produkt 1

HCID 86700075HCID 86700075, VerbindungAusbeute 81,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418807
HCID 178418807, Verbindung
Katalysator
HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3-Iodo-4-methoxypyridin-2-amine (350 mg), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (322 mg), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride-dichloromethane adduct (81 mg) and cesium fluoride (580 mg) were suspended in methanol (5.0 ml), and the suspension was heated under reflux at 80° C. for 19 hours. After leaving to cool, a saturated aqueous ammonium chloride solution was added, and the organic layer was extracted with ethyl acetate and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [ethyl acetate:dichloromethane:methanol=5:5:1 (v/v)] to give 245 mg of the title compound as a solid.

Aufarbeitung

  1. temperaturethe suspension was heated
  2. customAfter leaving
  3. temperatureto cool
  4. extractionthe organic layer was extracted with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography [ethyl acetate:dichloromethane:methanol=5:5:1 (v/v)]

Quellen und Nachweise

ORD-Eintrag
ord-8c244f861e66497b9fc123d87b1078ba
Quelldatensatz
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08933103B2

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