Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Bromobenzene | HCID 7961 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 86731572 | HCID 86731572 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 71522465 | HCID 71522465 | — |
Reaction Steps
A solution of (2-ethynylpiperidin-1-yl)(2-methyl-5-phenyl-1,3-thiazol-4-yl)methanone (25 mg, 0.081 mmol), bromobenzene (23 mg, 0.15 mmol), CuI (4.6 mg, 0.024 mmol), and triethylamine (0.15 mL, 1.1 mmol) in DMF (0.5 mL) was purged subsurface with nitrogen. Palladium tetrakis (9.3 mg, 0.0081 mmol) was added and the reaction was heated at 90° C. overnight. The reaction was stirred over excess Quadrapure TU overnight, then filtered and dried. The residue was subjected to purification via reverse phase HPLC to provide the title compound which gave a high resolution mass spectrum (ES+) m/z of 387.1527, calculated for M+H+ [C24H22N2OS: 387.1526].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08940898B2 |
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| Source dataset | uspto-grants-2015_01 |
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| ORD ID | ord-4183836fccd84df484f0f59a85ae7e60 |
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| Source note | uspto-grants-2015_01 |
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