Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | 2-Methyl-N-[2-(tetrahydro-2H-pyran-2-yl)-6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-2H-indazol-4-yl]-1,3-thiazole-4-carboxamide | HCID 58255833 | — |
| Reactant | N-(5-bromo-2-methoxypyridin-3-yl)-2,4-difluorobenzenesulfonamide | HCID 59859951 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 44541043 | HCID 44541043 | 15.5% |
Reaction Steps
N-[5-Bromo-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide (39 mg, 0.104 mmol), 2-methyl-N-[2-(tetrahydro-2H-pyran-2-yl)-6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-2H-indazol-4-yl]-1,3-thiazole-4-carboxamide (50 mg, 0.104 mmol), Pd(dppf)Cl2 (8 mg, 10.36 μmol) and sodium carbonate (44 mg, 0.415 mmol) were added to a microwave vial, followed by 1,4-Dioxane (0.5 mL) and Water (0.5 mL) and the reaction mixture was heated in the microwave at 140° C. for 20 min. After cooling, the mixture was then passed through a 1 g silica cartridge and washed with DCM:methanol. The solvent was evaporated by blow down under nitrogen. The residue was dissolved in 1.6 ml DMSO:methanol (1:1, v/v) and passed through a 1 g C18 cartridge, washing with acetonitrile, then evaporated by blow down. The residue was dissolved in 1.6 ml DMSO:methanol (1:1, v/v) and purified by MDAP (Method E). This MDAP purification step was then repeated to afford the title compound (9 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08163743B2 |
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| Source dataset | uspto-grants-2012_04 |
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| ORD ID | ord-f147a6111ef14501a9b1f2ebd4923315 |
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| Source note | uspto-grants-2012_04 |
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