Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-Fluorophenylboronic acid | HCID 285645 | — |
| Reactant | 4-(4-Bromophenyl)-4-cyclopropylmethoxy-1-phenylcyclohexanecarboxylic acid | HCID 68480045 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 59442699 | HCID 59442699 | 9.7% |
Reaction Steps
19 mg of tetrakis(triphenylphosphine)palladium(0) were added to a solution of 200 mg of 4-(4-bromophenyl)-4-cyclopropylmethoxy-1-phenylcyclohexanecarboxylic acid in 4 ml of degassed toluene under argon in a two-necked flask and the mixture was stirred for 10 min at room temperature. Subsequently, 65.1 mg of 4-fluorobenzeneboronic acid and 0.341 ml of a 2 M sodium carbonate solution were added and the reaction mixture was heated for 24 h at 100° C. After cooling, water and EA were added, the organic phase was separated and the aqueous phase was extracted twice with EA. The combined organic phases were dried over magnesium sulfate and the solvent was removed in vacuo. After purification of the residue by preparative HPLC, 20 mg of the title compound were obtained as a white lyophilizate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08076324B2 |
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| Source dataset | uspto-grants-2011_12 |
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| ORD ID | ord-31b87729e7b34da9801d2e23f51144ad |
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| Source note | uspto-grants-2011_12 |
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