Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Bromothiazole | HCID 76430 | — |
| Reactant | Sodium Bromide | HCID 253881 | — |
| Reactant | Potassium fluoride hydrate | HCID 23675105 | — |
| Reactant | HCID 67107706 | HCID 67107706 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | (Trifluoromethyl)benzene | HCID 7368 | — |
| Product | HCID 67107589 | HCID 67107589 | 19.5% |
Reaction Steps
A mixture of methyl 6-(benzenesulphonylmethyl)-2-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (Intermediate 59, 0.284 g), tetrakis-(triphenylphosphine) palladium (0.05 g), 2-bromothiazole (0.267 g), potassium fluoride monohydrate (0.25 g) and sodium bromide (0.117 g) in α,α,α-trifluorotoluene (5 ml) was degassed and then heated in the microwave at 175° C. for 2 hours. Ethyl acetate was added and the mixture was filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100% to give methyl 6-benzenesulphonylmethyl-2-methoxy-3-(thiazol-2-yl)-benzoate (0.05 g) as a brown oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09067905B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-552dfca6b174425491c83cc1d9603258 |
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| Source note | uspto-grants-2015_06 |
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