Cesium carbonate → HCID 59560273, compound

Participants

Reaction Conditions

Reaction Steps

Cs2CO3 (0.806 g, 2.47 mmol) was added to a solution of ethyl 4-hydroxy-2-methylbenzo[b]thiophene-6-carboxylate (0.275 g, 1.16 mmol) and 2,4-difluoro-N,N-dimethylbenzamide (0.269 g, 1.45 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 (0.19 g, 1.98 mmol) and HATU (0.664 g, 1.75 mmol) were added. The reaction mixture was stirred at 80° C. for one hour and then filtered. Purification by HPLC gave a solid (100 mg, 19% yield) as expected product. 1H NMR (400 MHz, CD3OD) δ 8.27 (s, 1 H) 7.54 (m, 1 H) 7.48 (m, 1 H) 7.34-7.38 (t, 1 H) 7.00 (s, 1 H) 6.82-6.89 (m, 2 H) 6.59-6.60 (m, 1 H) 3.81 (s, 3 H) 3.09 (s, 3 H) 2.97 (m, 3 H) 2.58 (m, 3 H). LCMS for C23H21FN4O3S m/z 453.10 (M+H)+.

Provenance & Evidence