HuagongsheHuagongshe Chemistry Print Report · For research reference only
5-(5-(benzyloxy)-6-(4-fluoro-1H-indol-2-yl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide → 5-(6-(4-fluoro-1H-indol-2-yl)-5-hydroxypyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 5-(5-(benzyloxy)-6-(4-fluoro-1H-indol-2-yl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide | HCID 71295469 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 5-(6-(4-fluoro-1H-indol-2-yl)-5-hydroxypyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide | HCID 71295471 | 57.7% |
Reaction Steps
A mixture of 5-(5-(benzyloxy)-6-(4-fluoro-1H-indol-2-yl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (120 mg, 0.173 mmol) and Pd/C (20 mg) in methanol (10 mL) was stirred under H2 atmosphere at room temperature for 1 hour. The mixture was then filtered through Celite and concentrated to provide 5-(6-(4-fluoro-1H-indol-2-yl)-5-hydroxypyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (60 mg, yield: 57.7%). 1H-NMR (Methanol-d4, 400 MHz) δ 7.95˜8.00 (m, 4H), 7.80 (s, 1H), 7.37 (t, J=8.8 Hz, 2H), 7.22˜7.30 (m, 4H), 6.64˜6.69 (m, 1H), 3.23 (s, 3H), 2.94 (s, 3H), 2.90 (s, 3H). MS (M+H)+: 603.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09265773B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-b4011c718e2d423a8a959a65b4fac5cb |
| Source note | uspto-grants-2016_02 |