2-Acetyl-5-bromothiophene → 1-{5-[2-(4-Isopropoxyphenoxy)-1,3-thiazol-5-yl]thien-2-yl}ethanone

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of Example 2A (550 mg, 1.05 mmol) in N,N-dimethyl formamide (10 mL) at room temperature, was added 1-(5-bromothiophen-2-yl)ethanone (269 mg, 1.31 mmol) followed by dichlorobis(triphenylphosphine)palladium(II) (45 mg, 0.064 mmol). The reaction mixture was heated at 60° C. overnight. The solvent was evaporated under vacuum and the product was purified via silica gel column chromatography using a gradient of 15 to 35% ethyl acetate in hexane to give the desired compound (320 mg). 1H NMR (300 MHz, CDCl3) δ ppm 7.56 (d, J=4.04 Hz, 1H) 7.43 (s, 1H) 7.15-7.24 (m, 2H) 7.02 (d, J=4.04 Hz, 1H) 6.88-6.97 (m, 2H) 4.44-4.62 (heptet, J=5.88 Hz, 1H) 2.54 (s, 3H) 1.36 (d, J=5.88 Hz, 6H). MS (ESI) m/z 360 (M+1)+.

Provenance & Evidence