Reaktion #168211

Reaktionsgleichung

3-chloro-5-(4-hydroxyphenyl)isonicotinonitrile

4-methoxyphenylboronic acid

pyridine

→

3-chloro-5-(4-(4-methoxyphenoxy)phenyl)isonicotinonitrile

Ausbeute 68.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe mixture was filtered through a CELITE® pad
2. 2
   Sonstigeto remove molecular
3. 3
   Waschensieves (rinsed with dichloromethane)
4. 4
   Sonstigequenched with saturated ammonium chloride (20 mL) and ammonium hydroxide (2 mL)
5. 5
   Extraktionextracted with dichloromethane (3×10 mL)
6. 6
   TrocknenThe combined extracts were dried (MgSO4)
7. 7
   Einengenconcentrated
8. 8
   Wascheneluting with 5-30% ethyl acetate in hexanes

Vorschrift

A mixture of 3-chloro-5-(4-hydroxyphenyl)isonicotinonitrile (50 mg, 0.217 mmol), 4-methoxyphenylboronic acid (132 mg, 0.867 mmol), copper(II) acetate (47.2 mg, 0.260 mmol), pyridine (0.140 mL, 1.734 mmol) and 4 A molecular sieves (300 mg) in dichloromethane (6 mL) was stirred under air at room temperature for 4 days. The mixture was filtered through a CELITE® pad to remove molecular sieves (rinsed with dichloromethane), quenched with saturated ammonium chloride (20 mL) and ammonium hydroxide (2 mL) and extracted with dichloromethane (3×10 mL). The combined extracts were dried (MgSO4) and concentrated. Silica gel chromatography, loading with toluene and eluting with 5-30% ethyl acetate in hexanes, gave 3-chloro-5-(4-(4-methoxyphenoxy)phenyl)isonicotinonitrile as a white solid (49.7 mg, 67% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.72 (1H, s), 8.68 (1H, s), 7.45-7.59 (2H, m), 6.99-7.14 (4H, m), 6.88-6.99 (2H, m), 3.83 (3H, s); MS (ES+) m/z: 337 (M+H); LC retention time: 4.321 min (analytical HPLC Method A).

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