Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide | HCID 68239402 | — |
| Reactant | HCID 137001383 | HCID 137001383 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Product | HCID 136339016 | HCID 136339016 | 26.1% |
Reaction Steps
To a stirring mixture of ethyl 6-bromopteridin-4(3H)-one (50 mg, 0.22 mmol), 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (110 mg, 0.22 mmol) and Na2CO3 (35 mg, 0.33 mmol) in dioxane/H2O (2 mL/0.2 mL) was added Pd(dppf)Cl2 (10 mg) under N2 protection. The mixture was stirred at 100° C. overnight. The mixture was concentrated in vacuo and extracted with EtOAc. After the organic layer was washed with brine, dried over Na2SO4, filtered and evaporated, the crude product was purified by prep-HPLC to give the product of 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4-oxo-3,4-dihydropteridin-6-yl)benzofuran-3-carboxamide (30 mg, yield: 26%). 1H-NMR (DMSO-d6, 400 MHz) δ 9.19 (s, 1H), 8.61 (d, J=4.8 Hz, 1H), 8.39 (s, 1H), 8.19 (s, 1H), 7.97˜7.99 (m, 3H), 7.42 (t, J=8.4 Hz, 2H), 3.37 (s, 3H), 3.00 (s, 3H), 2.83 (d, J=4.0 Hz, 3H). MS (M+H)+: 523.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09364482B2 |
|---|
| Source dataset | uspto-grants-2016_06 |
|---|
| ORD ID | ord-fa85618850dc4bfbb09682eabf508858 |
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| Source note | uspto-grants-2016_06 |
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