Dichloromethane → 1-(4-Amino-2-phenyl-thieno[3,2-c]pyridin-7-yl)-ethanone

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To a suspension of 1-(4-chloro-2-phenyl-thieno[3,2-c]pyridin-7-yl)-ethanone 97 (61 mg, 0.21 mmol) and potassium carbonate (174 mg, 1.26 mmol) in DMF (1.8 mL) was added 4-methoxybenzylamine (85 μl, 0.64 mmol). The resultant mixture was heated at 50° C. for 6.75 h. After this time, 20 mL of a 1:1 mixture of dichloromethane and methanol was added and the resultant slurry was filtered. The filtrate was concentrated and the residue was dissolved in trifluoroacetic acid (7 mL). The resultant mixture was heated at 55° C. for 2.75 h. After this time, the reaction mixture was concentrated and the residue was purified by silica gel column chromatography (eluent: dichloromethane:MeOH:Et3N, 98.5:1.5:0.5) to give 98. 1H NMR (400 MHz, CDCl3) δ: 2.66 (s, 3H), 5.78–6.15 (br s, 2H), 7.37 (t, J=7.0 Hz, 1H), 7.45 (t, J=7.5 Hz, 2H), 7.54 (s, 1H), 8.0 (d, J=3.5 Hz, 2H), 8.56 (s, 1H). MS (EI) m/z (M+H+) 269.

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