Sodium Carbonate → HCID 46941214, 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 4-(methylsulfonyl)phenylboronic acid (0.078 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 taken up in water, and the solid obtained was filtered off, washed with Et2O and dried. The crude product was suspended in CH3CN at 50° C., filtered off and dried in vacuo to afford the desired product (0.061 g, 57%). HPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.): tR=4.04 min, [M+H]+ m/z 440.0; 1H-NMR (DMSO-d6+TFA): δ=8.88 (1H, s), 8.36 (2H, d, J=8.4 Hz), 8.28 (1H, s), 8.17 (1H, s), 8.06 (2H, d, J=8.4 Hz), 3.24 (3H, s) ppm.

Provenance & Evidence