Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzaldehyde | HCID 240 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | HCID 68239709 | HCID 68239709 | — |
| Solvent | O-Xylene | HCID 7237 | — |
| Product | HCID 68239405 | HCID 68239405 | 175.1% |
Reaction Steps
A mixture of 2-(4-fluorophenyl)-5-(4-hydroxy-3-(1H-indol-2-yl)phenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (50 g, 0.08 mmol), PTSA (3.0 mg, 0.017 mmol), and benzaldehyde (42 mg, 0.41 mmol) in xylene (2 mL) was stirred at 130° C. for 2 h under microwave. Water was added, extracted with EtOAc, the organic layer was washed with brine, dried over Na2SO4. After concentrated, the resulting residue was purified using prep-TLC to provide the product of compound 63 (20 mg, yield: 38%). 1H-NMR (CDCl3, 400 MHz) δ 8.96 (s, 1H), 7.88˜7.92 (m, 2H), 7.76 (s, 1H), 7.65 (s, 1H), 7.50 (s, 1H), 7.32˜7.47 (m, 6H), 7.14˜7.17 (m, 4H), 6.96˜6.99 (m, 2H), 6.86 (s, 1H), 6.55 (s, 1H), 5.91 (d, J=4.8 Hz, 1H), 3.02 (s, 3H), 2.98 (d, J=4.8 Hz, 3H), 2.94 (s, 3H). MS (M+H)+: 672.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09265773B2 |
|---|
| Source dataset | uspto-grants-2016_02 |
|---|
| ORD ID | ord-cbfcfb33e6b3465393caa4017d4c1577 |
|---|
| Source note | uspto-grants-2016_02 |
|---|