Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride) | HCID 2734660 | — |
| Reactant | HCID 10613176 | HCID 10613176 | — |
| 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 22032907 | HCID 22032907 | 23.4% |
Reaction Steps
1-Benzyl-7-(3-chloro-4-fluorophenyl)-1H-indole was prepared by coupling 1-benzyl-7-bromo-1H-indole (0.691 g, 2.41 mmol), and 3-chloro-4-fluorophenylboronic acid (0.538 g, 3.09 mmol), using [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.0628 g, 0.0769 mmol), and potassium carbonate (0.502 g, 3.63 mmol) in dioxane (18 mL) and water (1.8 mL) following the procedure described in Step 1 of Example 11. Purification by HPLC using 1.5% ethyl acetate in hexane as the mobile phase furnished the title compound as a clear gum (0.189 g, 23%). 1HNMR (300 MHz, DMSO-d6): δ 7.65 (d, 1H, J=7.5 Hz), 7.5 (s, 1H), 7.3 (t, 1H, J=8.3 Hz), 7.05-7.2 (m, 6H), 6.85 (d, 1H, J=7.5 Hz), 6.65 (d, 1H, J=3.8 Hz), 6.3-6.4 (m, 2H), and 4.95-5.2 ppm (m, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07368471B2 |
|---|
| Source dataset | uspto-grants-2008_05 |
|---|
| ORD ID | ord-9e4343533a0f41809d570da1385ea19a |
|---|
| Source note | uspto-grants-2008_05 |
|---|
