Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | N-(6-bromo-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide | HCID 58255750 | — |
| Reactant | HCID 58255798 | HCID 58255798 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 58255738 | HCID 58255738 | — |
Reaction Steps
N-(6-Bromo-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide (50 mg, 0.148 mmol), Pd(dppf)Cl2 (12 mg, 0.015 mmol), 2 M sodium carbonate (aq) (0.222 ml, 0.444 mmol), 1,4-dioxane (1 ml) and water (1 ml) were added to 1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanesulfonamide (53 mg, 0.178 mmol). The reaction was heated in a Biotage microwave at 150° C. for 15 mins. The reaction mixture was extracted with DCM (2×20 ml) and the separated, combined organic layer was evaporated to dryness. The residue was dissolved in MeOH:DMSO (1 ml, 1:1, v/v) and purified by MDAP (Method B). Appropriate fractions were dried under a stream of nitrogen to give title compound, 5 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-dd7eb1313d1143d38815f53985c19855 |
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| Source note | uspto-grants-2012_04 |
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