HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 595651Generated: October 29, 2026
Sodium Carbonate → 5-bromo-2-(4-formylphenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide
https://huagongshe.com/reaction/595651
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-Formylphenylboronic Acid | HCID 591073 | — |
| Reactant | 5-bromo-2-iodo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide | HCID 90332469 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-bromo-2-(4-formylphenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide | HCID 90332488 | 58.1% |
Reaction Steps
To a degassed solution of 5-bromo-2-iodo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (400 mg, 0.82 mmol), (4-formylphenyl) boronic acid (110 mg, 0.74 mmol) and Na2CO3 (174 mg, 1.6 mmol) in DMF (4 mL) was added Pd(dppf)Cl2 (20 mg) under N2, and the mixture was stirred at 100° C. for 2 h. After the solvent was removed, the residue was purified by column chromatography (DCM:EtOAc=10:1) to give the product of 5-bromo-2-(4-formylphenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (200 mg, yield: 52%). 1H-NMR (CDCl3, 400 MHz) δ 10.09 (s, 1H), 8.09˜8.15 (m, 3H), 8.02 (s, 2H), 7.75 (s, 1H), 5.90 (br s., 1H), 3.36 (s, 3H), 3.11 (s, 3H), 3.05 (d, J=4.8 Hz, 3H). MS (M+H)+: 465/467.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09243002B2 |
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| Source dataset | uspto-grants-2016_01 |
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| ORD ID | ord-ff30215eca7e46309d2b80e9a8db3429 |
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| Source note | uspto-grants-2016_01 |
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