(what is upscale? posh? trendy? looking for cocktail drinks? wine? beer?)
There's no upscale bar in that area; it's the university 'hood (and is right smak in the middle of nightly protests, nice spectator sport, but no good bar in the area, expect for a couple of beer places )
You could try the Jello (martini) Bar (151 Rue Ontario Est).
Other than that, up the street (20minutes safe walk), there's Le Lab (1351 Rachel, Est ) or maybe Barmacie (laurier st.); or maybe Pullman (wine bar) or Phillips Lounge( 1184 Place Phillips )
But in general, for upscale, your best bets is to go to hotel bars (St-James, Ritz, ) one of the better is "Suite 701" at hotel Place d'armes.
they have a lot of fancybars on peel street including champagne bars set up for grand prix festivities and although student and other protests went around site this evening police made sure they didnt get onto peel grand prix site or side corridors going to site. There will be the upscale cars on display on Peel as well to enjoy. You might enjoy this more than other bars closer to your hotel.
St Catherine and st Denis is not an attractive area in the city......many problems and I am not referring to students. T bar has some cocktails and you can sit outside on terrace, but tables may not be available as francofolies festival also on this weekend in area of t bar. There is a bar at top of hotel on this festival site where you can have drinks on rooftop terrace - place des arts metro stop, but the fancier places are listed above.