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Sodium Carbonate → HCID 68008562, Verbindung

HRID 333922
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 333922
Br[C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:10][N:11]([CH3:21])[C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.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>[CH3:10][N:11]([CH3:21])[C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:3]=[C:4]([CH3:9])[C:5]([NH2:8])=[N:6][CH:7]=2)=[CH:14][CH:13]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 1379342-Amino-5-bromo-3-methylpyridineHCID 27343444-(Dimethylamino)phenylboronic acid

Produkt 1

HCID 68008562HCID 68008562, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 1140
Toluene
Lösungsmittel

Versuchsvorschrift

A solution of 5-bromo-3-methylpyridin-2-amine (120a, 1.87 g, 10.0 mmol) in toluene (60 mL) was treated with 4-(dimethylamino)phenylboronic acid (2.48 g, 15.0 mmol), Pd(PPh3)4 (345 mg, 0.30 mmol), and 2M Na2CO3(aq) (10 mL). The reaction mixture was heated to reflux for 18 hours and then cooled to room temperature. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4(s) and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give 5-(4-(dimethylamino)phenyl)-3-methylpyridin-2-amine (120b).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 18 hours
  3. customThe reaction mixture was quenched with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4(s)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-365f46db4bad427e8ff160f84716bbd4
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08883793B2

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