HCID 69417337, compound → HCID 69420062, compound

Participants

Reaction Steps

5-Fluoro-6-(2-fluoro-4-vinyl-phenylamino)-3-methyl-3H-benzoimidazole-5-carboxylic acid methyl ester (1.5 g, 4.35 mmol) was combined with 10% palladium/carbon (0.4 g) in tetrahydrofuran (50 mL). The resultant solution was hydrogenated at 4295 psi for 56 min. The reaction mixture was filtered and concentrated in vacuo to afford 0.91 g. Recrystallization from dichlormethane-hexane afforded pure 6-(4-Ethyl-2-fluoro-phenylamino)-5-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid methyl ester, m.p. 238° C.; 1H NMR (400 MHz, CD3OD) δ 8.28 (s, 1 H), 8.24 (br s, 1 H), 8.10 (s, 1 H), 6.93 (dd, J=12.4, 1.5 Hz, 1 H), 6.80 (brd, J=8.3 Hz, 1 H), 6.61 (td, J=8.6,5.4 Hx, 1 H), 3.94 (s,3 H), 3.92 (s, 3 H), 2.55 (q, J=5.6 Hz, 2 H), 1.20 (t, J=5.6 Hz, 3 H). Anal. Calcd/Found for C18H15F2N3O2: C, 62.60/62.11; H, 4.96/4.80; N, 12.15, 11.80.

Provenance & Evidence