P-Toluenesulfonamide → N-(6-(2-(4-methylphenylsulfonamido)pyridin-4-yl)benzo[d]thiazol-2-yl)acetamide

Participants

Reaction Steps

A microwave vial equipped with a magnetic stir bar was charged with 4-methylbenzenesulfonamide (0.170 g, 0.99 mmol) in DMF (3 ml). Then sodium hydride (0.047 g, 2.0 mmol) was added into the mixture and allowed to stir an additional 15 minutes. Then N-(6-(2-chloropyridin-4-yl)benzo[d]thiazol-2-yl)acetamide (0.120 g, 0.40 mmol), palladium(II) acetate (0.0089 g, 0.040 mmol) and Xantphos (0.010 g) was added to the mixture. The vial was capped and placed into a CEM Microwave for 20 minutes at 120° C., while 100 watts of energy was supplied via Powermax® (Simultaneous heating while cooling technology). The progress of the reaction was monitored by LC/MS, which showed desired product in the mixture. The mixture was placed into a round-bottom flask, then diluted with ethyl acetate (20 ml) and stirred 20 minutes. The precipitate was collected by filtration and then purified by reverse-phase HPLC. This gave N-(6-(2-(4-methylphenylsulfonamido)pyridin-4-yl)benzo[d]thiazol-2-yl)acetamide (0.012 g, 6.9% yield) as a tan crystalline solid. MS (ESI pos. ion) m/z: 439 (MH+). Calc'd exact mass for C21H18N4O3S2: 438. 1H NMR (400 MHz, DMSO-d6): 2.07 (s, 3H), 2.28 (s, 3H), 6.69 (s, 1H), 6.91 (s, 1H), 7.15 (d, J=6.53 Hz, 2H), 7.44 (d, J=8.03 Hz, 1H), 7.56 (d, J=7.53 Hz, 1H), 7.68 (d, J=7.03 Hz, 2H), 7.90 (s, 2H).

Provenance & Evidence