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Potassium Carbonate → 3-(4-Aminophenyl)-5-{4-[(2R)-1,4-dioxan-2-ylmethoxy]-3-methoxyphenyl}pyridin-2-amine

HRID 1428106
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Reaktionsgleichung von HRID 1428106
Br[C:2]1[C:3]([NH2:24])=[N:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C@H:16]3[CH2:21][O:20][CH2:19][CH2:18][O:17]3)=[C:10]([O:22][CH3:23])[CH:9]=2)[CH:7]=1.CC1(C)C(C)(C)OB([C:33]2[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=2)O1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C(Cl)(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:37][C:36]1[CH:38]=[CH:39][C:33]([C:2]2[C:3]([NH2:24])=[N:4][CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([O:14][CH2:15][C@H:16]4[CH2:21][O:20][CH2:19][CH2:18][O:17]4)=[C:10]([O:22][CH3:23])[CH:9]=3)[CH:7]=2)=[CH:34][CH:35]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 867000583-Bromo-5-{4-[(2R)-1,4-dioxan-2-ylmethoxy]-3-methoxyphenyl}pyridin-2-amine

Produkt 1

HCID 867000573-(4-Aminophenyl)-5-{4-[(2R)-1,4-dioxan-2-ylmethoxy]-3-methoxyphenyl}pyridin-2-amineAusbeute 60,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 962WaterLösungsmittel
HCID 6212ChloroformLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

The compound obtained in Step 2 of Example 41 (2.05 g), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.14 g), tetrakis(triphenylphosphine)palladium (0.3 g), and potassium carbonate (2.15 g) were suspended in dioxane (30 ml) and water (6 ml), and the suspension was stirred at 100° C. for two hours. After leaving to cool, the reaction solution was diluted with chloroform, followed by washing with water. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [ethyl acetate:hexane=1:1->chloroform:ethanol=19:1 (v/v)] to give 1.27 g of the title compound as a solid.

Aufarbeitung

  1. customAfter leaving
  2. temperatureto cool
  3. washby washing with water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography [ethyl acetate:hexane=1:1->chloroform:ethanol=19:1 (v/v)]

Quellen und Nachweise

ORD-Eintrag
ord-fba96663e57a4a37a12a7c48235c44d9
Quelldatensatz
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08933103B2

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