Phenyl heterocycles as cox-2 inhibitors

A process of making a compound of formula XXXIII ##STR216## wherein R.sup.1 is selected from the group consisting of (a) S(O).sub.2 CH.sub.3, (b) S(O).sub.2 NH.sub.2, (c) S(O).sub.2 NHC(O)CF.sub.3, (d) S(O)(NH)CH.sub.3, (e) S(O)(NH)NH.sub.2, (f) S(O)(NH)NHC(O)CF.sub.3, (g) P(O)(CH.sub.3)OH, and (h) P(O)(CH.sub.3)NH.sub.2, R.sup.2 is selected from the group consisting of (a) mono-, di- or tri-substituted phenyl wherein the substituent is selected from the group consisting of (1) hydrogen, (2) halo, (3) C.sub.1-6 alkoxy, (4) C.sub.1-6 alkylthio, (5) CN, (6) CF.sub.3, (7) C.sub.1-6 alkyl, (8) N.sub.3, (9) --CO.sub.2 --C.sub.1-4 alkyl, (10) --C(R.sup.5)(R.sup.6)--OH, (11) --C(R.sup.5)(R.sup.6)--O--C.sub.1-4 alkyl, and (12) --C.sub.1-6 alkyl-CO.sub.2 --R.sup.5 ; (b) mono-, di- or tri-substituted heteroaryl wherein the heteroaryl is a monocyclic aromatic ring of 5 atoms, said ring having one hetero atom which is S, O, or N, and optionally 1, 2, or 3 additionally N atoms, or the heteroaryl is a monocyclic ring of 6 atoms, said ring having one hetero atom which is N, and optionally 1, 2, or 3 additional N atoms; said substituents are selected from the group consisting of (1) hydrogen, (2) halo, including fluoro, chloro, bromo and iodo, (3) C.sub.1-6 alkyl, (4) C.sub.1-6 alkoxy, (5) C.sub.1-6 alkylthio, (6) CN, (7) CF.sub.3, (8) N.sub.3, (9) --C(R.sup.5)(R.sup.6)--OH, and (10) --C(R.sup.5)(R.sup.6)--O--C.sub.1-4 alkyl; R.sup.5 and R.sup.6 are each independently selected from the group consisting of (a) hydrogen, (b) C.sub.1-6 alkyl, or R.sup.5 and R.sup.6 together with the carbon to which they are attached form a saturated monocyclic carbon ring of 3, 4, 5, 6 or 7 atoms, comprising reacting a substituted aryl bromomethyl ketone of formula XXXII ##STR217## with a substituted aryl acetic acid of the following formula ##STR218## in the presence of a base and treating the resulting product with 1,8-diazabicyclo›5.4.0!undec-7-ene to yield a compound of formula XXXIII.