Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 6-Bromoindole | HCID 676493 | — |
| Reactant | 4,4,5,5-Tetramethyl-2-(2-methyl-5-nitrophenyl)-1,3,2-dioxaborolane | HCID 17750269 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | N,N-Dimethylformamide--water (1/1) | HCID 21962138 | — |
| Product | HCID 67205348 | HCID 67205348 | 64.8% |
Reaction Steps
6-Bromo-1H-indole (203 mg, 1.04 mmol) and potassium carbonate (287 mg, 2.08 mmol) was dissolved in a DMF/water (4:1, 2.5 mL) mixture solution, and the gas included in the mixture solution was removed using ultrasonic wave and nitrogen gas. After sequentially adding 4,4,5,5-tetramethyl-2-(2-methyl-5-nitrophenyl)-1,3,2-dioxaborolane (300 mg, 1.14 mmol) and Pd(dppf)Cl2 (85 mg, 0.10 mmol), the mixture was stirred at room temperature in a sealed reactor. 2 hours later, after adding ethyl acetate and water, the reaction solution was filtered through a diatomite pad. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was dried with anhydrous magnesium sulfate and then concentrated. Purification of the residue by chromatography (silica gel, EA:Hx=1:4) yielded 6-(2-methyl-5-nitrophenyl)-1H-indole (170 mg) as brown solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08765749B2 |
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| Source dataset | uspto-grants-2014_07 |
|---|
| ORD ID | ord-a1c7a106305947a0aa75a3a7c44c133b |
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| Source note | uspto-grants-2014_07 |
|---|
