Reaktion #587201

Reaktionsgleichung

1-(4-iodophenyl)indolin-4-ol

1-fluoro-4-nitrobenzene

4-methoxy-1H-indole

Cs2CO3

→

4-methoxy-1-(4-nitrophenyl)-1H-indole

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeis provided in Reaction Scheme 4b

Vorschrift

The synthesis of 1-(4-iodophenyl)indolin-4-ol (92) is provided in Reaction Scheme 4b. The reaction of 1-fluoro-4-nitrobenzene and 4-methoxy-1H-indole in the presence of Cs2CO3 gave 4-methoxy-1-(4-nitrophenyl)-1H-indole (88), which was reduced with H2/Pd to yield 4-(4-methoxy-1H-indol-1-yl)benzenamine (89). The amino group of 89 was converted via the Sandmeyer reaction to 1-(4-iodophenyl)-4-methoxy-1H-indole (90) which on reduction with sodium borocyanohyride gave 1-(4-iodophenyl)-4-methoxyindoline (91). The indoline 91 was demethylated with BBr3 to provide the desired 92.

Quelle