Hydrochloric Acid → 5-Benzyloxy-pyridin-2-ylamine hydrochloride

HRID 335163

Reaktionsgleichung

Reaktionsgleichung von HRID 335163
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](C)(C)[N-:18][Si](C)(C)C.[Li+].Cl.C(=O)(O)[O-].[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1COCC1>[ClH:15].[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH2:18])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 2733832Lithium HexamethyldisilazideHCID 100137175-(Benzyloxy)-2-chloropyridine

Produkt 1

HCID 669951705-Benzyloxy-pyridin-2-ylamine hydrochlorideAusbeute 98,94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a nitrogen purged solution of mL Pd2 (dba)3 (10.19 g, 11.12 mmol), 5-(benzyloxy)-2-chloropyridine (48.87 g, 222.5 mmol), (2-diphenyl)dicyclohexyl-phosphine (7.797 g, 22.25 mmol) and THF (700 mL) was added lithium hexamethyl disilazide (267.0 mL, 267.0 mmol). The reaction was heated at 65° C. overnight and cooled to ambient temperature. 1M HCl (250 mL) was added and stirred for minutes. Saturated sodium bicarbonate was added slowly. The mixture was extracted several times with CH2Cl2, dried, filtered, and concentrated to give the title compound (52.1 g, 98.94% yield).

Aufarbeitung

  1. temperaturecooled to ambient temperature
  2. extractionThe mixture was extracted several times with CH2Cl2
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-df42bb9ffab44f3180050693d20fa6f0
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883828B2

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