Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 5-Bromonicotinonitrile | HCID 736793 | — |
| Reactant | 1-Ethynyl-3-(trifluoromethyl)benzene | HCID 2778490 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178419050 | HCID 178419050 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67047454 | HCID 67047454 | 43% |
Reaction Steps
Add triethylamine (1.93 mL, 13.64 mmol), copper (I) iodide (37.3 mg, 0.190 mmol) and bis(triphenylphosphine)palladium (II) dichloride (120 mg, 0.170 mmol) to a solution of 5-bromonicotinonitrile (624 mg, 3.41 mmol) and 1-ethynyl-3-trifluoromethylbenzene, (prepared essentially as described in PREPARATION 13), (580 mg, 3.41 mmol) in ethyl acetate (3 mL). Stir in a sealed tube at 50° C. for 18 h, concentrate and purify by silica gel chromatography, eluting with 100:0 to 0:100 hexanes:ethyl acetate to give the title compound (400 mg, 43%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07915424B2 |
|---|
| Source dataset | uspto-grants-2011_03 |
|---|
| ORD ID | ord-4462817597da404685019c586b3f8fe8 |
|---|
| Source note | uspto-grants-2011_03 |
|---|
