Sodium Carbonate → HCID 46941215, compound

Participants

Reaction Steps

3-(trifluoromethyl)-5-(5-iodoimidazo[2,1-b][1,3,4]thiadiazol-2-yl)pyridin-2-amine (0.100 g, 0.243 mmol, 1 eq) was dissolved in dioxane (1.5 mL), then 2-fluoropyridine-5-boronic acid (0.055 g, 0.389 mmol, 1.6 eq) was added followed by 2M aq. Na2CO3 (0.5 mL, 4 eq). The suspension was degassed (N2, 15 min) and equipped with an argon balloon. Pd(Ph3P)2Cl2 (0.043 g, 0.061 mmol, 0.25 eq) was quickly added, and the reaction flask was placed in a pre-heated bath (115° C.). After stirring at reflux temperature for 3 h the mixture was cooled to RT and concentrated. The residue was suspended in EtOAc and water, and the clear water phase was removed. The remainder was concentrated to dryness and triturated with Et2O, filtered off, washed with Et2O and dried in vacuo to afford the desired product (0.049 g, 53%). HPLC-MS (5-100% B in 8 min at 0.8 mL): tR=5.14 min, [M+H]+ m/z 381.0; 1H-NMR (DMSO-d6): δ=8.93 (1H ,bs), 8.84 (1H, bs), 8.67-8.58 (1H, m), 8.24 (1H, bs), 7.92 (1H, s), 7.42-7.34 (3H, m) ppm

Provenance & Evidence