Cesium carbonate → 2-[5-(3-Amino-5-methylphenyl)-1,3-thiazol-2-yl]propane-2-sulfonamide

Participants

Reaction Conditions

Reaction Steps

2-(5-Bromo-1,3-thiazol-2-yl)propane-2-sulfonamide (1.223 g, 4.29 mmol), 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.00 g, 4.29 mmol), tris(dibenzylideneacetone)-dipalladium(0) (0.196 g, 0.214 mmol), X-phos (0.204 g, 0.429 mmol), and cesium carbonate (4.19 g, 12.87 mmol) were combined in a flask, sealed and purged with N2 (3×). Degassed dioxane (15 mL) and water (1.5 mL) were added and the reaction mixture was heated at 100° C. for 16 hrs. The reaction was diluted with water and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4) and evaporated. Flash chromatography (SiO2, dry load, gradient elution 0 to 75% EtOAc in CH2Cl2) afforded 2-[5-(3-amino-5-methylphenyl)-1,3-thiazol-2-yl]propane-2-sulfonamide (0.302 g, 0.97 mmol, 22.6% yield) as a tan foam. MS ESI: [M+H]+ m/z 312.1. 1H NMR (500 MHz, DMSO-d6) δ 7.92 (s, 1H), 6.99 (m, 2H), 6.59 (m, 2H), 6.34 (s, 1H), 5.18 (br s, 2H), 2.15 (s, 3H), 1.75 (s, 6H).

Provenance & Evidence