Sodium Carbonate → HCID 57933030, compound

Participants

Reaction Conditions

Reaction Steps

To a microwave pressure tube is added 0.100 g (0.254 mmol) of 8-(1-ethyl-propyl)-3-[2-bromo-4-methyl-5-thiazolyl]-2,6-dimethyl-imidazo[1,2-b]pyridazine, 0.157 g (0.762 mmol) of 4-(trifluoromethoxy)benzene boronic acid, 0.147 g (0.127 mmol) of Pd(PPh3)4, 0.381 mL (0.762 mmol) of 2 M aqueous sodium carbonate, and 2 mL Ethanol. The reaction mixture is heated in the microwave at 160° C. for up to 1 hour. The reaction mixture is partitioned between 50 mL of ethyl acetate and 50 mL of water. The layers are separated and the aqueous is extracted 3×50 mL of ethyl acetate, dried (MgSO4), and concentrated under vacuum. The crude mixture is purified by chromatography using 2% methanol in dichloromethane as a solvent system. The product containing fractions are combined to obtain 0.085 g of the product, 70% yield. MS, ES+=475.2 (M+1); 1H-NMR (DMSO-d6)=8.134-8.112 (d, 2H); 7.553-7.532 (d, 2H); 7.059 (s, 1H); 3.142-3.113 (m, 1H); 2.500 (s, 3H); 2.399 (s, 3H); 2.330 (s, 3H); 1.907-1.782 (m, 4H); 0.827-0.791 (m, 6H) ppm.

Provenance & Evidence