Reaktion #7856

Reaktionsgleichung

4-(1,3-benzoxazol-2-yl)-2-cyanophenyl trifluoromethanesulfonate

2-tri-n-butylstannylpyridine

EtOAc

→

5-(1,3-benzoxazol-2-yl)-2-pyridin-2-yl benzonitrile

Lösungsmittel

DME

brine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to rt
2. 2
   WaschenThe organic layer was washed with brine (2×20 mL)
3. 3
   Trocknendried (MgSO4)
4. 4
   Sonstigethe crude material was purified on flash column (silica gel, hexanes:EtOAc 3:1)

Vorschrift

The degassed solution of 4-(1,3-benzoxazol-2-yl)-2-cyanophenyl trifluoromethanesulfonate (300 mg, 1.2 mmol) in DME (5 mL) was added 2-tri-n-butylstannylpyridine (273 mg, 0.74 mmol), tetrakis(triphenylphosphine)palladium(0) (150 mg, 0.1 mmol). The reaction was stirred at 90° C. overnight and cooled to rt. EtOAc (100 mL) was added, as well as brine (50 mL). The organic layer was washed with brine (2×20 mL), dried (MgSO4), and the crude material was purified on flash column (silica gel, hexanes:EtOAc 3:1) to afford desired 5-(1,3-benzoxazol-2-yl)-2-pyridin-2-yl benzonitrile as pinkish solid. 1H NMR (CD3OD, 300 MHz), δ 8.85 (d 1H), 8.72 (d, 1H), 8.59 (m, 1H), 8.08 (d, 1H), 7.91 (d, 2H), 7.85 (m, 1H), 7.65 (m, 1H), 7.45 (m, 3H). MS (ESI) 298 (M+H)+.

Quelle