Process for preparing indole carboxamide compounds

A process for preparing a compound of Formula (V):

• comprising the steps of:
• (a) reacting a compound of Formula (I) and a compound of Formula (II):
• to provide a compound of Formula (III):
• and
• (b) converting said compound of Formula (III) to said compound of Formula (V) by steps (b1), (b2), and (b3), in any order:
• (b1) forming an indole group by reaction with a compound of Formula (IVa) or a compound of Formula (IVb):
• (b2) converting said —NR4R5 group to —NH2;
• and
• (b3) converting said —OR3 group to —NH2+;
• wherein:
• X1 is halo, —NO2, —OS(O)2R, or —N2+;
• X2 is Cl, Br, I, —OH, —OS(O)2R, acyloxy, or trialkylsiloxy;
• R1 and R2 are independently selected from H, benzyl, substituted benzyl, 4-methoxyphenyl, acyl, —S(O)2Ar, tert-butoxycarbonyl, or benzyloxycarbonyl;
• R3 is H, C1-8 alkyl, aryl, or heteroaryl;
• R4 and R5 are independently selected from H, benzyl, 4-methoxybenzyl, 4-methoxyphenyl, acyl, —S(O)2R, tert-butoxycarbonyl, or benzyloxycarbonyl;
• R8 is H, C1-3 alkyl, or aryl;
• and
• each R is independently C1-3 alkyl or aryl.