Cesium carbonate → 4-(4-(Dimethylcarbamoyl)-3-fluorophenoxy)-N-(1-methyl-1H-pyrazol-3-yl)benzofuran-6-carboxamide

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Reaction Conditions

Reaction Steps

Cs2CO3 (0.806 g, 2.47 mmol) was added to a solution of ethyl 4-hydroxy-benzofuran-6-carboxylate (8a) (0.256 g, 1.24 mmol) and 2,4-difluoro-N,N-dimethylbenzamide (0.287 g, 1.55 mmol) in DMF (5 mL). The mixture was stirred at 150° C. for 8 hours and then cooled to room temperature. 1-Methyl-1H-pyrazol-3-amine (0.21 g, 2.11 mmol) and then HATU (0.71 g, 1.87 mmol) were added. The reaction mixture was stirred at 50° C. for one hour and then filtered. Purification by HPLC gave a solid (200 mg, 39% yield) as the expected product. 1H NMR (400 MHz, DMSO-d6) δ 10.95 (s, 1 H) 8.22 (s, 1 H) 8.16 (m, 1 H)) 7.62-7.36 (s, 1 H) 7.60-7.61 (m, 1 H) 7.39-7.43 (m, 1 H) 7.08-7.11 (m, 1 H) 6.95-6.97 (m, 1 H) 6.89 (s, 1 H) 6.59-6.60 (m, 1 H) 3.78 (s, 3 H) 2.99 (s, 3 H) 2.88 (m, 3 H). LCMS for C22H19FN4O4 m/z 423.10 (M+H)+.

Provenance & Evidence