Key indicatorsSingle-crystal X-ray study T = 293 K Mean '(C±C) = 0.006 A Ê Disorder in main residue R factor = 0.046 wR factor = 0.089 Data-to-parameter ratio = 16.8For details of how these key indicators were automatically derived from the article, seeThe title compound, C 11 H 10 BrNO 2 S, crystallizes in a columnar structure consisting of interdigitated CÐHÁ Á ÁO doubly bonded chains. The columns pack in a herring-bone fashion and are linked through additional weak hydrogen bonding. The structure is very nearly isomorphous to one in which the bromo substituent on the pyrrole ring is replaced by a chloromethyl group, in spite of the difference in size, shape and interactions involving these two groups.

2-Bromo-N-(p-toluenesulfonyl)pyrrole (2), a crystalline stable derivative of 2-bromopyrrole (1) has been prepared in 80% yield by bromination of pyrrole, followed by conversion to the N-(p-toluenesulfonyl) derivative. This compound is stable indefinitely at ambient temperature. Compound 2 is an excellent substrate for Suzuki coupling with arylboronic acids.Several years ago our group described the synthesis and pharmacology of a series of N-alkyl-3-(1-naphthoyl)pyrroles which are ligands for the cannabinoid central nervous system (CB 1 ) receptor. 1 Relative to similarly substituted cannabimimetic indoles, these compounds show at best modest affinity for the CB 1 receptor and have corresponding diminished potency in vivo. 1,2 Both these indoles and pyrroles were designed on the basis of a hypothesis that the 3-acyl group which is present in these compounds is involved in a hydrogen bonding interaction with the receptor. 1,2 However, subsequent experiments have provided convincing evidence that the 3-acyl group is not essential for binding to the CB 1 receptor and suggest that cannabimimetic indoles and indenes interact with the receptor primarily by aromatic stacking. 3 This hypothesis suggested that N-alkyl-2-aryl-4-(1-naphthoyl)pyrroles should have greater receptor affinity than the N-alkyl-3-(1-naphthoyl)pyrroles reported previously due to the presence of an additional aromatic ring.

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