2,3-Dinitrotoluene → 4-Aminoindole

Participants

Reaction Steps

Scheme 4 illustrates the production of a compound of Formula (In) in which R99 is an indole compound and R7, R8, R9, R10, R11, R12, R28, R29 and R30 are defined as above for Formula (III). A piperidin-4-one compound of Formula (XIVa) is produced as described above in Scheme 3. A dinitro-toluene compound of Formula (XVI) is reacted with N,N-dimethylformamide dimethyl acetal and pyrrolidine under conditions effective to bring about cyclization, thereby providing an indol-4-ylamine compound of Formula (XVII). The compound of Formula (XVII) is then reacted with a bis(2-chloroethyl)-benzylamine under conditions effective to produce the compound of Formula (XVIII). The compound of Formula (XVIII) is then reacted under conditions effective to remove the benzyl protecting group to produce a 4-piperazin-1-yl-indole of Formula (XIX). The piperazin-1-yl-indole compound of Formula (XIX) is then reacted with the piperidin-4-one compound of Formula (XIVa) as described above in Scheme 1 to produce the piperazine-piperidine compound of Formula (XX), which is a compound of Formula (III).

Provenance & Evidence