Br[C:2]1[S:6][C:5]([NH:7][C:8](=[O:10])[CH3:9])=[N:4][C:3]=1[CH3:11].[CH:12]([C:14]1[O:18][C:17](B(O)O)=[CH:16][CH:15]=1)=[O:13].C(=O)(O)[O-].[Na+].O>CN1C(=O)CCC1.[Pd](Cl)Cl>[CH:12]([C:14]1[O:18][C:17]([C:2]2[S:6][C:5]([NH:7][C:8](=[O:10])[CH3:9])=[N:4][C:3]=2[CH3:11])=[CH:16][CH:15]=1)=[O:13]
To a solution of 3.0 g of N-(5-bromo-4-methylthiazol-2-yl)acetamide in 50 mL of NMP was added 3.0 g of 5-formylfuran-2-ylboronic acid. To the stirred solution was then added 300 mg of 1,1 bis-(diphenylphosphino)-ferrocene) palladium dichloride followed by 10 mL of saturated sodium bicarbonate. The resulting biphasic mixture was irradiated at 150° C. in a microwave for 20 min. The resulting mixture was poured into 200 mL of water and filtered. The filtrate was extracted with ether and the ether layers were combined, dried over sodium sulfate and concentrated. The resulting oil was precipitated with methylene chloride and filtered, yielding 1.2 g of N-(5-(5-formylfuran-2-yl)-4-methylthiazol-2-yl)acetamide as an orange solid which was used without further purification. LC/MS: 251.07 (M+H)/2.18 min.
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