Benzenesulfonamide, N,4-dimethyl- → N-(6-(2-(N,4-dimethylphenylsulfonamido)pyridin-4-yl)benzo[d]thiazol-2-yl)acetamide

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Reaction Steps

A microwave vial equipped with a stir bar was charged with n-methyl-p-toluenesulfonamide (0.26 g, 1.4 mmol) in DMF (3 ml). Then sodium t-butoxide (0.270 g, 2.8 mmol) was added to the mixture and allowed to stir 5 minutes. Then palladium(II) acetate (0.013 g, 0.057 mmol), N-(6-(2-chloropyridin-4-yl)benzo[d]thiazol-2-yl)acetamide (0.173 g, 0.57 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 100° 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 peaks. The mixture was diluted with DMSO and purified by reverse-phase HPLC. This gave N-(6-(2-(N,4-dimethylphenylsulfonamido)pyridin-4-yl)benzo[d]thiazol-2-yl)acetamide (0.010 g, 3.9% yield) as a tan solid. MS (ESI pos. ion) m/z: 453 (MH+). Calc'd exact mass for C22H20N4O3S2: 452. 1H NMR (300 MHz, DMSO-d6): 2.03 (s, 3H), 2.37 (s, 3H), 3.24 (s, 3H), 7.32-7.42 (d, 2H), 7.44-7.73 (m, 6H), 7.80 (s, 1H), 8.14 (s, 1H), 8.29 (d, 1H).

Provenance & Evidence