Iodobenzene diacetate

Example 107

[Figure (not displayed)]

0.050 g (0.30 mmol) of 4-methylthieno[3,2-b]pyrrole-5-carbaldehyde (Aldrich, Cat. N. CDS015804), 0.033 g (0.30 mmol) of o-phenylendiamine (Aldrich, Cat. N. P23938-5G) and iodobenzene diacetate (Aldrich, Cat. N. 178721-25G) were stirred at −15° C. in solvent free conditions. The mixture was then warmed to RT becoming a sticky brown oil. After stirring at RT for 1.5 h a further portion of 0.018 g (0.18 mmol) of o-phenylendiamine was added. The obtained dark oil was purified by column chromatography on silica gel (EtOAc/hexane 3:97, v:v to 30:70 v:v) to provide 0.025 g of 5-(1H-benzimidazol-2-yl)-4-methyl-thieno[3,2-b]pyrrole (33%). ¹H NMR (DMSO-d₆) δ (ppm): 12.74-12.57 (bs, 1H), 7.68-7.46 (m, 2H), 7.44-7.39 (m, 1H), 7.28-7.22 (m, 1H), 7.21-7.14 (m, 3H), 4.26 (s, 3H); MS (ESI): m/z: 254 [M+H]⁺.

Example 107

[Figure (not displayed)]

0.050 g (0.30 mmol) of 4-methylthieno[3,2-b]pyrrole-5-carbaldehyde (Aldrich, Cat. N. CDS015804), 0.033 g (0.30 mmol) of o-phenylendiamine (Aldrich, Cat. N. P23938-5G) and iodobenzene diacetate (Aldrich, Cat. N. 178721-25G) were stirred at −15° C. in solvent free conditions. The mixture was then warmed to RT becoming a sticky brown oil. After stirring at RT for 1.5 h a further portion of 0.018 g (0.18 mmol) of o-phenylendiamine was added. The obtained dark oil was purified by column chromatography on silica gel (EtOAc/hexane 3:97, v:v to 30:70 v:v) to provide 0.025 g of 5-(1H-benzimidazol-2-yl)-4-methyl-thieno[3,2-b]pyrrole (33%). ¹H NMR (DMSO-d₆) δ (ppm): 12.74-12.57 (bs, 1H), 7.68-7.46 (m, 2H), 7.44-7.39 (m, 1H), 7.28-7.22 (m, 1H), 7.21-7.14 (m, 3H), 4.26 (s, 3H); MS (ESI): m/z: 254[M+H]⁺.