Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Thiazole | HCID 9256 | — |
| Reactant | 2-Bromo-5-nitroanisole | HCID 101293 | — |
| Reactant | Potassium Acetate | HCID 517044 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 68629712 | HCID 68629712 | 59% |
Reaction Steps
In a microwave vial, a mixture of 2-bromo-5-nitroanisole (300 mg, 1.27 mmol), potassium acetate (188 mg, 1.90 mmol) and tetrakis(triphenylphosphine)palladium(0) (74 mg, 0.634 mmol) in 4 ml dimethyl acetamide was flushed with argon. Thiazole (459 uL, 6.34 mmol) was added, the tube was sealed, and the mixture was heated for 1 h to 160° C. in a microwave oven. The mixture was diluted with ethyl acetate and water, the layers were separated and the aqueous layer was extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and evaporated under reduced pressure. The residual material was subjected to column chromatography on silica gel using heptane/ethyl acetate (7:3) as eluent to afford the title compound as yellow solid (177 mg, 59%). Mp 125-128° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08962834B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-93c9ce8ca0704bea878630a53a38016c |
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| Source note | uspto-grants-2015_02 |
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