Cesium carbonate → HCID 74220870, compound

Participants

Reaction Steps

To a solution of N-(2,4-dimethoxybenzyl)-6-fluoro-1-(2-iodobenzyl)-N-(1,2,4-thiadiazol-5-yl)-1H-indazole-5-sulfonamide (2-3, 0.068 g, 0.103 mmol, 1.0 equiv) in THF (0.94 mL) was added (E)-tert-butyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-en-1-yl)carbamate (0.088 g, 0.310 mmol, 3.0 equiv) and Pd(Cl)2dppf (0.008 g, 10.34 μmol, 0.1 equiv) followed by 1M cesium carbonate (0.094 mL) and the system was irradiated at 120° C. for 10 min. The reaction contents were extracted with EtOAc and water and the organic phase was dried over Na2SO4, filtered and concentrated. To this residue was added DCM (0.69 mL) followed by TFA (0.17 mL) and the system was stirred at room temperature for 1 h. The reaction contents were then concentrated in vacuo and purified by reverse phase chromatography (10%→70% 0.1% TFA in ACN: 0.1% TFA in water) to yield compound Ex-5 as a mono TFA salt. 1H NMR (400 MHz, CDCl3) δ 8.30-8.43 (m, 3H), 8.00 (br s, 2H), 7.80 (m, 1H), 7.50 (m, 1H), 7.18-7.39 (m, 3H), 6.80 (m, 1H), 6.20 (m, 1H), 5.70 (s, 2H), 2.45 (m, 3H). HRMS [M+H] C19H17FN6O2S2 calc'd 445.0911. found 445.0910.

Provenance & Evidence