Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 59463772 | HCID 59463772 | — |
| Reactant | HCID 86040733 | HCID 86040733 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178419050 | HCID 178419050 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59463785 | HCID 59463785 | 44% |
Reaction Steps
A mixture of 330 mg (0.88 mmol) of 1,1,1-trifluoro-2-(6-methanesulfonyl-4-methylchroman-4-ylmethyl)pent-4-yn-2-ol, 270 mg (0.88 mmol) of trifluoromethanesulfonic acid 4-cyano-2-methyl-6-nitrophenyl ester, 310 mg (0.04 mmol) of bis(triphenylphosphine)palladium (II) dichloride, 17 mg (0.09 mmol) of copper (I) iodide, and 0.25 mL of anhydrous triethylamine in 2 mL of THF was warmed at 60° C. in a sealed tube in the microwave. After 20 minutes, the mixture was adsorbed onto CELITE® filter aid and chromatographed on silica gel eluting with ethyl acetate-hexanes (gradient: 0-30% EtOAc) to afford 205 mg (44%) of 3-methyl-5-nitro-4-[5,5,5-trifluoro-4-hydroxy-4-(6-methanesulfonyl-4-methylchroman-4-ylmethyl)pent-1-ynyl]benzonitrile as a brown oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07795272B2 |
|---|
| Source dataset | uspto-grants-2010_09 |
|---|
| ORD ID | ord-c7884d4c7a2f4b9c88850447e6ad4b97 |
|---|
| Source note | uspto-grants-2010_09 |
|---|
