6-Methoxy-2-pyridinecarbonitrile → 1-(6-Methoxypyridin-2-YL)cyclopropan-1-amine

HRID 1040425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1040425
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]#[N:10])[CH:6]=[CH:5][CH:4]=1.[CH3:11][CH2:12][Mg+].[Br-]>C1COCC1.O.CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C>[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2([NH2:10])[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=1

Komponenten

6

Edukt 2

HCID 130236446-Methoxy-2-pyridinecarbonitrileHCID 178461630HCID 178461630, Verbindung

Produkt 1

HCID 584310411-(6-Methoxypyridin-2-YL)cyclopropan-1-amineAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178460666HCID 178460666, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 6-methoxy-pyridine-2-carbonitrile (1.50 g, 11.2 mmol) in THF (75 mL) at room temperature was added Ti(OiPr)4 (7.21 mL, 24.6 mmol). EtMgBr (14.9 mL, 44.7 mmol) was added dropwise. and the clear brown solution became heterogeneous. The reaction mixture was stirred for 1 h at room temperature. The reaction was diluted with water (10 mL), extracted with EtOAc (3×25 mL) and dried with MgSO4. After filtration, the solvent was removed in vacuo. The residue was purified by reverse phase HPLC to afford 380 mg (22%) of 1-(6-methoxy-pyridin-2-yl)-cyclopropylamine, m/z 166.3 [M+1]+.

Aufarbeitung

  1. extractionextracted with EtOAc (3×25 mL)
  2. dry with materialdried with MgSO4
  3. filtrationAfter filtration
  4. customthe solvent was removed in vacuo
  5. customThe residue was purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-1950563d887f4ddea8e40216adfeccc5
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552205B2

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