Process for large-scale production of indolyl alkyl pyrimidinyl

Details Process for large-scale production of indolyl alkyl pyrimidinyl Process for large-scale production of indolyl alkyl pyrimidinyl

1994-11-08

1996-08-27

Shah, Mukund J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

C07D40314

Patent

active

055502393

ABSTRACT:
An improved, novel convergent process suitable for large scale preparation of the antimigraine agent 4-(5-methoxy-4-pyrimidinyl)-1-[3-[5-[[(methylamino)sulfonyl]methyl]-1H-ind ol-3-yl]propyl]piperazine (BMS 180048) and close analogs. The improved process provides efficiencies in handling, purification, and product yield and involves a novel heteroannulation reaction that provides the indole ring moiety and propylpiperazinyl-pyrimidine backbone in a single step.

REFERENCES:
patent: 5300506 (1994-04-01), Smith et al.
Larock et al, "Synthesis of Indoles via Palladium-Catalyzed Heteroannulation of Internal Alkynes," Journal of American Chemical Society, 1991, 113, pp. 6689-6690.

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