Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3,5-Difluoroaniline | HCID 96595 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | HCID 86606579 | HCID 86606579 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86606578 | HCID 86606578 | 8.4% |
Reaction Steps
A microwave vial was charged with 5-bromo-2-methyl-thiazole-4-carboxylic acid (2-hydroxymethyl-pyridin-4-yl)-amide (0.135 g, 0.411 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) (0.81 g, 0.140 mmol) and palladium dibenzylideneacetone (Pd2dba3)-chloroform complex (0.044 g, 0.043 mmol). Degassed dioxane (10 ml) was added, followed by 3,5-difluoroaniline (0.064 g, 0.496 mmol) and cesium carbonate (0.271 g, 0.831 mmol) The vial was then irradiated in a microwave oven at 150° C. for 40 min. The mixture was diluted with THF and the solids filtered, washing with THF. The filtrate was evaporated and the residue purified by flash chromatography on silica gel with dichloromethane/methanol 100:0→90:10 gradient to yield the title compound (0.013 g, 8%) as an off-white solid, MS (ISP): m/e=377.4 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07678815B2 |
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| Source dataset | uspto-grants-2010_03 |
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| ORD ID | ord-244231b3463a44f6a902e2fca15aebbf |
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| Source note | uspto-grants-2010_03 |
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