Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Phenylboronic Acid | HCID 66827 | — |
| Reactant | 4-(2-Amino-4-methyl-phenylsulfanyl)-phenol | HCID 66808123 | — |
| Catalyst | Cupric acetate | HCID 8895 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 66808413 | HCID 66808413 | 98% |
Reaction Steps
The product from Example 6c (0.500 g, 1.91 mmol) was dissolved in CH2Cl2 along with phenyl boronic acid (0.701 g, 5.74 mmol), copper(II) acetate (0.659 g, 3.83 mmol), and triethylamine (0.387 g, 3.83 mmol). Stirred at room temperature for 48 h, at which time 2 more equivalents of each reagent was added. Stirred at room temperature for another 16 h at which time another 2 eq of each reagent was added. Stirred at room temperature for another 16 h. The reaction was diluted with water and extracted with ethyl acetate Dried over Na2SO4, filtered and concentrated under vacuum giving the crude product which was purified silica gel column chromatography eluting with 20% EtOAc/hexane (0.100 g, 15%). The product was reduced with SnCl2 following the procedure from Example 5I to give the title compound (90 mg, 98%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07915411B2 |
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| Source dataset | uspto-grants-2011_03 |
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| ORD ID | ord-0ec1732eeaee40c9931b350747e8f793 |
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| Source note | uspto-grants-2011_03 |
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