2-Amino-5-methylpyridine → 4-(4-(Dimethylcarbamoyl)-3-fluorophenoxy)-N-(5-methylpyridin-2-yl)benzofuran-6-carboxamide

Participants

Reaction Steps

The title compound was prepared in a similar manner as described for Example 341, from ethyl 4-hydroxy-benzofuran-6-carboxylate (8a) (0.26 g, 1.24 mmol), 2,4-difluoro-N,N-dimethylbenzamide (0.287 g, 1.55 mmol), and 2-amino-5-methyl pyridine (0.228 g, 2.11 mmol) (except that amide coupling was carried out at 75° C. for four hours) to give a solid (81 mg, 15% yield) as the expected product. 1H NMR (400 MHz, DMSO-d6) δ 10.84 (s, 1 H) 8.27 (s, 1 H) 8.22-8.23 (m, 1 H) 8.18-8.19 (m, 1 H)) 8.06-8.08 (d, 1 H) 7.67 (m, 1 H) 7.64 (m, 1 H) 7.39-7.44 (t, 1 H) 7.09-7.12 (m, 1 H) 6.95-6.97 (m, 1 H) 6.90 (m, 1 H) 3.00 (s, 3 H) 2.88 (m, 3 H) 2.28 (s, 3 H). LCMS for C24H20FN3O4 m/z 434.10 (M+H)+.

Provenance & Evidence