Process for the preparation of 3-phenylpyrrole derivatives

Details Process for the preparation of 3-phenylpyrrole derivatives Process for the preparation of 3-phenylpyrrole derivatives

1989-10-11

1990-09-18

Brust, Joseph Paul

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548531, 548537, 548539, 548540, 548561, C07D20702

Patent

active

049580302

ABSTRACT:
3-Phenylpyrrole derivatives of formula I ##STR1## wherein X is cyano, --CO--R.sub.3, --CO--OR.sub.3 or ##STR2## R.sub.1 and R.sub.2 are each independently of the other hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, nitro, cyano, halogen or C.sub.1 -C.sub.6 haloalkyl, or
R.sub.1 and R.sub.2, when taken together, are methylenedioxy or difluoromethylenedioxy,
R.sub.3 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, phenyl or benzyl, or phenyl or benzyl which are each substituted by halogen, methyl, methoxy or methylthio, and
R.sub.4 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, phenyl or benzyl, or phenyl or benzyl which are each substituted by halogen, methyl, methoxy or methylthio,
are prepared by
(a) reacting N-(p-tolylsulfonyl)methyl formamide, in an inert solvent and in the presence of an organic base, with phosphoroxy chloride, mixing the reaction solution with water, separating the aqueous phase of the resultant two-phase mixture, and
(b) reacting the organic phase containing (p-tolylsulfonyl)methyl isocyanide direct with a compound of formula II ##STR3## wherein X, R.sub.1 and R.sub.2 are as defined for formula I, Y is --CO--NHR.sub.4, --CO--R.sub.5 or --S--R.sub.5, R.sub.5 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, phenyl or benzyl, or phenyl or benzyl which are each substituted by halogen, methyl, methoxy or methylthio, and R.sub.4 is as defined for formula I, in the presence of a base.

REFERENCES:
patent: 4680413 (1987-07-01), Genda et al.
patent: 4705801 (1987-11-01), Martin et al.
patent: 4778901 (1988-10-01), Martin

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