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Potassium Phosphate, Tribasic → 2-Amino-5-cyclopropylpyridine

HRID 451442
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 451442
Br[C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH:9]1(B(O)O)[CH2:11][CH2:10]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:9]1([C:2]2[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=2)[CH2:11][CH2:10]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 706222-Amino-5-bromopyridineHCID 2760897Cyclopropylboronic acid

Produkt 1

HCID 230048692-Amino-5-cyclopropylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962
Water
Lösungsmittel
2×
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 5-bromo-pyridin-2-ylamine (2 g, 11.55 mmol) and cyclopropyl boronic acid (2.98 g, 34.68 mmol) in toluene (40 mL) and water (2 mL) was added K3PO4 (8.59 g, 40.46 mmol) under an argon atmosphere. To this were added Pd(OAc)2 (259.52 mg, 1.16 mmol) and tricyclohexylphosphene (647.3 mg, 2.3 mmol) and stirred at 80° C. for 16 hours. The reaction mixture was cooled to room temperature and water was added. The aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate/hexane as eluent. The title compound was obtained as an off white solid (1.1 g, 71%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. dry with materialthe combined organic phases were dried over sodium sulfate
  4. customthe solvent was evaporated
  5. customthe residue purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ed57d874183d410cbac3c01e1f17fd78
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08486967B2

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