Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-(Trifluoromethyl)phenylboronic acid | HCID 2734389 | — |
| Reactant | 1-Benzyl-4-bromo-1H-indole | HCID 22032943 | — |
| 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 22032904 | HCID 22032904 | 49.1% |
Reaction Steps
1-Benzyl-4-[4-(trifluoromethyl)phenyl]-1H-indole was prepared by coupling of 1-benzyl-4-bromo-1H-indole (0.428 g, 1.50 mmol), and 4-trifluoromethylphenylboronic acid (0.374 g, 1.97 mmol), using [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.0638 g, 0.0781 mmol), and potassium carbonate (0.416 g, 3.01 mmol) in dioxane (15 mL) and water (1.5 mL) following the procedure described in Step 1 of Example 11. Purification by flash chromatography (Biotage apparatus) using hexane as an eluant yielded the title compound as a yellow gum (0.259 g, 49%). 1HNMR (300 MHz, DMSO-d6): δ 7.8-7.95 (m, 4H), 7.65 (d, 1H, J=3 Hz), 7.55 (d, 1H, J=7.5 Hz), 7.15-7.35 (m, 7H), 6.65 (d, 1H, J=3 Hz), and 5.5 ppm (s, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07368471B2 |
|---|
| Source dataset | uspto-grants-2008_05 |
|---|
| ORD ID | ord-471db62fd6c4439da947964193633fe1 |
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| Source note | uspto-grants-2008_05 |
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