2-Bromo-3-nitropyridine → 7-Bromo-6-azaindole

Participants

Reaction Steps

The route shown in Scheme 1 below exemplifies synthesis of certain 7-aryl(heteroaryl) and 7-anilino-6-azaindole-1-sulfonamide compounds of the present invention. 2-Bromo-3-nitropyridine (1) reacts with vinylmagnesium bromide in THF, at −40-50° C. to afford 7-Bromo-6-azaindole (2), which reacts with 4-methoxyphenylsulfonyl chloride to provide 7-bromo-1-(4-methoxyphenylsulfonyl)-1H-pyrrolo[2,3-c]pyridine (3). The sulfonamide (3), is then either treated with a substituted or unsubstituted phenylboronic acid, Pd(PPh3)4, and K2CO3 in toluene/EtOH to afford final compound (4) or treated with a substituted or unsubstituted aniline in pyridine to yield final compound (5).

Provenance & Evidence