Reacción #166174

Ecuación de reacción

oxindole

4-chlorobenzonitrile

potassium carbonate

2,2,7,7-tetramethyl-1-(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphepane

→

4-(2-Oxoindolin-1-yl)benzonitrile

Rendimiento 71.0%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroIn a nitrogen-atmosphere glovebox, a microwave vial equipped with a magnetic stir bar
2. 2
   OtroThe vial was sealed with a crimp top
3. 3
   Otroplaced in a heating block at 80° C
4. 4
   Otrothe vial was removed from the heating block
5. 5
   workup.ADDITIONThe reaction solution was diluted with tetrahydrofuran (2 mL)
6. 6
   Filtraciónfiltered into a tared 125-mL Erlenmeyer flask
7. 7
   LavadoThe vial was rinsed with tetrahydrofuran (2×2.5 mL)
8. 8
   Lavadoby washing of the filter cake with tetrahydrofuran (5 mL)

Procedimiento

In a nitrogen-atmosphere glovebox, a microwave vial equipped with a magnetic stir bar was charged with oxindole (40 mg, 0.300 mmol, 1 equivalent), 4-chlorobenzonitrile (50 mg, 0.361 mmol, 1.2 equivalents), potassium carbonate (83 mg, 0.601 mmol, 2 equivalents), tris(dibenzylideneacetone)dipalladium(0) (Pd2dba3) (2.8 mg, 0.0030 mmol, 0.01 equivalents) and 2,2,7,7-tetramethyl-1-(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphepane (3.0 mg, 0.0066 mmol, 0.022 equivalents). Then tetrahydrofuran (0.3 mL) was syringed into the vial. The vial was sealed with a crimp top and placed in a heating block at 80° C. After 24 hours, the vial was removed from the heating block, cooled to room temperature and brought out of the glovebox. The reaction solution was diluted with tetrahydrofuran (2 mL) and filtered into a tared 125-mL Erlenmeyer flask. The vial was rinsed with tetrahydrofuran (2×2.5 mL), followed by washing of the filter cake with tetrahydrofuran (5 mL). A wt % analysis was performed on the filtered solution and an assay yield of 71% was measured (literature reference: Altman R A, et al. J. Am. Chem. Soc. 2008; 130: 9613-9620). 1H NMR (400 MHz, CDCl3) δ ppm 7.90-7.82 (m, 2H), 7.68-7.60 (m, 2H), 7.41-7.34 (m, 1H), 7.32-7.25 (m, 1H), 7.21-7.13 (m, 1H), 6.93 (dd, J=9.8, 2.1 Hz, 1H), 3.79 (s, 2H).

Fuente