Preparation of vincadifformine

Details Preparation of vincadifformine Preparation of vincadifformine

C - Chemistry, Metallurgy

07

D

260/241.15

C07D 487/04 (2006.01) C07C 41/48 (2006.01) C07C 41/56 (2006.01) C07C 43/313 (2006.01) C07C 43/315 (2006.01) C07D 471/04 (2006.01) C07D 471/20 (2006.01)

Patent

CA 1098903

ABSTRACT OF THE DISCLOSURE The invention relates to the preparation of vincadifformine. Tetrahydro-.beta. -carboline (II) is reacted with benzoyl chloride to provide 2-benzoyl-1,2,3,4- tetrahydro-9H-pyrido-[ 3,4b]-indole (III). Then compound (III) is reduced to give 2-benzyl-1,2,3,4-tetrahydro-9H-pyri- do [3,4b]-indole (IV). Thereafter, compound (IV) is transformed by t-butyl hypochlorite into chloroindolenine derivative (V) which is immediately treated with thallium t-butyl methyl malonate to give t-butyl methyl 3-benzyl- 1,2,3,4,5,6-hexahydroazepion-[ 4,5b]-indole-5,5-dicarboxy- late (VI). Compound (VI) is then partly decarboxylated into methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino-[ 4,5b] - indole-5-caxboxylate (VII). Compound (VII) is hydrogenated to give methyl 1,2,3,4,5,6-hexahydroazepino-[ 4,5 b] -indole- 5-carboxylate (IX). In an alternative embodiment, com- pound (VI) can be hydrogenated to methyl t-butyl 1,2,3,4, 5,6-hexahydroazepino-[ 4,5b]-indole-5,5-dicarboxylate (VIII) which is then decarboxylated into compound (IX). Compound (IX) is condensed with 1-bromo-4-formyl-hexane to yield vincadifformine (I). - 1 -

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