Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3,5-Bis-trifluoromethylphenylboronic acid | HCID 156265 | — |
| Reactant | 1-Benzyl-5-Bromo-1H-Indole | HCID 285756 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 22032962 | HCID 22032962 | 51.2% |
Reaction Steps
1-Benzyl-5-[3,5-bis(trifluoromethyl)phenyl]-1H-indole was prepared by coupling 1-benzyl-5-bromo-1H-indole (1.44 g, 5.03 mmol), and 3,5-bis-(trifluoromethyl)phenylboronic acid (1.63 g, 6.32 mmol), using [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.211 g, 0.258 mmol), and potassium carbonate (1.38 g, 9.98 mmol) in dioxane (54 mL) and water (5.4 mL) following the procedure described in Step 1 of Example 11. The reaction mixture was heated to 85° C. for 3 hours. Purification by HPLC using 10% methylene chloride in hexane as the mobile phase furnished the title compound as a light yellow solid (1.08 g, 51%), mp: 90-95° C. 1HNMR (200 MHz, DMSO-d6): δ 8.3 (s, 2H), 8.1 (s, 1H), 8.0 (s, 1H), 7.6 (s, 3H), 7.15-7.4 (m, 5H), 6.6 (d, 1H, J=2.6 Hz), and 5.5 ppm (s, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07368471B2 |
|---|
| Source dataset | uspto-grants-2008_05 |
|---|
| ORD ID | ord-43235f81b6864d5cab5c090c9b4e2dac |
|---|
| Source note | uspto-grants-2008_05 |
|---|
