Sodium Carbonate → N-(6-(2-(4-methoxyphenylsulfonyl)thiazol-5-yl)benzo[d]thiazol-2-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

5-Bromo-2-(4-methoxyphenylsulfonyl)thiazole (134.8 mg, 4.034 mmol), N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamide (163.6 mg, 0.5141 mmol), sodium carbonate (0.40 mL, 2.0 M in water, 0.80 mmol), and palladiumtetrakis(triphenyl phosphine) (59.5 mg, 51.5 μmol) were suspended in 1,4-dioxane (3.2 mL) and the reaction mixture was stirred and heated at 80° C. for 1.5 hours. Additional Pd(PPh3)4 (78 mg) was added to the mixture and stirring and heating were continued at 90° C. for another 90 minutes, at which time the reaction was cooled to RT. The organic phase was decanted, and the residual solid was washed with DCM and MeOH and filtered through a Celite® (diatomaceous earth) pad. This pad was washed with DCM and MeOH, and the filtrate was combined with the decanted suspension and concentrated. The solid was treated with Et2O and filtered. Solid washed with Et2O and purified on HPLC (10% to 95% MeCN/water with 0.1% TFA over 40 minutes) to afford N-(6-(2-(4-methoxyphenylsulfonyl)thiazol-5-yl)benzo[d]thiazol-2-yl)acetamide. MS (ESI pos. ion) m/z: 446. Calculated exact mass for C19H15N3O4S3: 445. 1H NMR (400 MHz, DMSO-d6): 12.51 (s, 1H), 8.48 (s, 1H), 8.45 (s, 1H), 7.99 (d, J=9.0 Hz, 2H), 7.81 (m, 2H), 7.22 (d, J=8.5 Hz, 2H), 3.87 (s, 3H), 2.22 (s, 3H).

Provenance & Evidence