1,2-Dimethoxyethane → HCID 57932995, compound

Participants

Reaction Steps

To a microwave pressure tube is added 0.070 g (0.178 mmol) of 8-(1-ethyl-propyl)-3-[2-bromo-4-methyl-5-thiazolyl]-2,6-dimethyl-imidazo[1,2-b]pyridazine, 0.066 g (0.534 mmol) of pyridine-3-boronic acid, 0.103 g (0.089 mmol) of Pd(PPh3)4, 0.267 mL (0.534 mmol) of 2 M aqueous Na2CO3, and 1 mL 7:3:2 DME:H2O:EtOH, and the mixture is heated at 160° C. for 60 min. The reaction mixture is partitioned between 25 mL of ethyl acetate and 25 mL of water. The layers are separated and the aqueous is extracted 3×25 mL of ethyl acetate, dried (MgSO4), and concentrated under vacuum. The crude mixture is purified by chromatography using hexanes/Ethyl acetate as a solvent system. The product containing fractions are combined to obtain 0.045 g of the product, 64% yield. MS, ES+=392.2 (M+1); 1HNMR (DMSO-d6) δ 9.18 (s, 1H); 8.65 (m, 1H); 8.34 (d, 1H); 7.60 (m, 1H); 7.06 (s, 1H); 3.06 (m, 1H); 2.50 (s, 3H); 2.40 (s, 3H); 2.34 (s, 3H); 1.87-1.82 (m, 4H); 0.83-0.79 (m, 6H) ppm.

Provenance & Evidence