1-Bromo-2-nitrobenzene → 7-Bromoindole

Participants

Reaction Steps

Similarly, the route shown in Scheme 2 below exemplifies synthesis of certain 7-aryl(heteroaryl)-indoline(indole)-1-sulfonamide compounds of the present invention. To synthesize indole-1-sulfonamide compound (9), 1-bromo-2-nitrobenzene (6) is reduced to afford 7-bromo-1H-indole (7), which reacts with 4-methoxyphenylsulfonyl chloride to provide 7-bromo-1-(4-methoxyphenylsulfonyl)-1H-indole (8). The sulfonamide (8), is then treated with an aryl or heteroaryl boronic acid, Pd(PPh3)4, and K2CO3 in toluene/EtOH to afford final compound (9). To synthesize indoline-1-sulfonamide compound (12), 7-bromo-1H-indole (7) is further reduced (with NaCNBH3 and CH3COOH, at room temperature) to afford 7-bromoindoline (10), which reacts with a substituted phenylsulfonyl chloride to provide bromo-indoline-sulfonamide (11). The bromo-indoline-sulfonamide (11) is then treated with an aryl or heteroaryl boronic acid, Pd(PPh3)4, and K2CO3 in toluene/EtOH to afford final compound (12), which can be further modified to obtain compound (13).

Provenance & Evidence