Cesium carbonate → HCID 59559853, 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. 2-Amino-5-methylpyridine (0.214 g, 2 mmol) and HATU (0.67 g, 1.75 mmol) were added. The reaction mixture was stirred at 75° C. for four hours and then filtered. Purification by HPLC gave a solid (92 mg, 17% yield) as expected product. 1H NMR (400 MHz, DMSO-d6) δ 10.79 (s, 1 H) 8.52 (s, 1 H) 8.21 (m, 1 H) 8.06-8.08 (d, 1 H) 7.68 (m, 1 H) 7.64-7.67 (m, 1 H) 7.37-7.41 (t, 1 H) 7.12 (s, 1 H) 7.02-7.06 (m, 1 H) 6.87-6.90 (m, 1 H) 2.99 (s, 3 H) 2.87 (s, 3 H) 2.59-2.60 (m, 3 H) 2.28 (s, 1 H). LCMS for C25H22FN3O3S m/z 464.10 (M+H)+.

Provenance & Evidence