Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 4-Methylbenzenethiol | HCID 7811 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 46203835 | HCID 46203835 | — |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Catalyst | Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1) | HCID 11029508 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 57624607 | HCID 57624607 | 89.2% |
Reaction Steps
A solution of N-{5-[2-(4′-bromo-2′-fluorobiphenyl-4-yl)ethyl]-2,2-dimethyl-1,3-dioxan-5-yl}acetamide (1.17 g) of Reference Example 10, 4-methylbenzenethiol (316 mg), diisopropylethylamine (672 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (67.3 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) (77.5 mg) in 1,4-dioxane (10 mL) was heated under reflux for 8 hr under a nitrogen atmosphere. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound (1.12 g) as pale-yellow crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08114902B2 |
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| Source dataset | uspto-grants-2012_02 |
|---|
| ORD ID | ord-caa77e8881a4454ca4449be7c67748f1 |
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| Source note | uspto-grants-2012_02 |
|---|
