5-Bromo-3-fluoropyridine-2-carbonitrile → 5-Cyclopropyl-3-fluoropicolinonitrile
Reaktionsgleichung
Br[C:2]1[CH:3]=[C:4]([F:10])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[Br-].[CH:12]1([Zn+])[CH2:14][CH2:13]1>C1COCC1.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>[CH:12]1([C:2]2[CH:3]=[C:4]([F:10])[C:5]([C:8]#[N:9])=[N:6][CH:7]=2)[CH2:14][CH2:13]1Komponenten
5
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To solution of 5-bromo-3-fluoropicolinonitrile (603 mg, 3.0 mmol) and Pd(PPh3)4 (173 mg, 0.15 mmol) in 10 mL of THF was added cyclopropyl zinc bromide (0.5 M, 10 mL) under N2. After being heated 80° C. for 4 h, the mixture was cooled to room temperature and quenched with sat. NH4Cl (aq). The mixture was extracted with EtOAc (3×) and the combined organic layers were washed with sat. NaHCO3 (aq.) and brine, dried (MgSO4), and concentrated. The crude product was purified by silica gel chromatography (elution with 0-8% EtOAc/Hex) to afford 5-cyclopropyl-3-fluoropicolinonitrile (406 mg).
Aufarbeitung
- temperaturethe mixture was cooled to room temperature
- customquenched with sat. NH4Cl (aq)
- extractionThe mixture was extracted with EtOAc (3×)
- washthe combined organic layers were washed with sat. NaHCO3 (aq.) and brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customThe crude product was purified by silica gel chromatography (elution with 0-8% EtOAc/Hex)
Quellen und Nachweise
- ORD-Eintrag
- ord-259dd783d5f442fb8351b0401bd06b6b
- Quelldatensatz
- uspto-grants-2014_05
- Patentnummer
- US08729071B2
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