Sodium Carbonate → HCID 57584970, compound

Participants

Reaction Conditions

Reaction Steps

N-(6-Chloropyridin-2-yl)benzenesulfonamide (0.480 g, 1.90 mmol) was dissolved in 1,4-dioxane (6 mL). Then N-(6-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)benzo[d]thiazol-2-yl)acetamide (0.7 g, 2 mmol), 2M Na2CO3 (2 mL, 4 mmol), and tetrakis(triphenylphosphine)palladium (0) (0.3 g, 0.2 mmol) was added to the mixture. The flask was fit with a reflux condensor, then placed into a pre-heated (95° C.) bath and allowed to stir under inert atmosphere overnight. The flask was removed from the heat bath and allowed to cool to ambient temperature. The mixture was filtered through a fritted funnel and the crude filtrate was purified by reverse-phase HPLC. This gave N-(6-(2-aminobenzo[d]thiazol-6-yl)pyridin-2-yl)benzenesulfonamide. MS (ESI pos. ion) m/z: 383 (MH+). Calculated exact mass for C18H14N4O2S2: 382. 1H NMR (400 MHz, acetone-d6): 8.19 (s, 1H), 8.08 (d, J=8.0 Hz, 2H), 7.86 (d, J=8.0 Hz, 1H), 7.74 (t, J=8.0 Hz, 1H), 7.53-7.64 (m, 4H), 7.44 (d, J=8.5 Hz, 1H), 7.13 (d, J=8.0 Hz, 1H), 6.98 (br s, 1H).

Provenance & Evidence