Use of 4-substituted 2-butanones to prepare nabumetone

Details Use of 4-substituted 2-butanones to prepare nabumetone Use of 4-substituted 2-butanones to prepare nabumetone

1996-04-09

1997-02-04

Reamer, James H.

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

Organic compounds

Oxygen containing

568314, 568315, 568316, C07C 4562

Patent

active

056000090

ABSTRACT:
The palladium-catalyzed coupling of aryl and vinyl halides with vinylic compounds is disclosed. A preferred embodiment relating to the palladium catalyzed coupling of 4-substituted and 6-substituted-2-methoxynaphthalene to form nabumetone is also disclosed. The beauty of this novel reaction is that methylvinylketone, normally employed by the art directly as-is for the preparation of nabumetone, is formed in situ. We have discovered a mechanism to take advantage of the in situ formation of methylvinylketone, thus avoiding the use of expensive, toxic, and unstable methyl vinyl ketone feed. This reaction may be employed for a variety of pharmaceutically active and non-pharmaceutical compounds.

REFERENCES:
patent: 4061779 (1977-12-01), Lake et al.
patent: 4221741 (1980-09-01), Gaster
patent: 4420639 (1983-12-01), Lake et al.
patent: 5225603 (1993-07-01), Aslam et al.
"Convenient Syntheses of Nabumetone," Aslam et al.; Synthesis Communications, 869, 1989.

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