HuagongsheHuagongshe Chemistry Print Report · For research reference only
Piperidine → 3-Piperidin-1-yl-1-triisopropylsilanyl-1H-indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Reactant | 2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl | HCID 2734217 | — |
| Reactant | 3-Bromo-1-(triisopropylsilyl)indole | HCID 10991769 | — |
| Reactant | 3-Morpholin-4-yl-1-triisopropylsilanyl-1H-indole | HCID 58975176 | — |
| Catalyst | Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1) | HCID 11029508 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-Piperidin-1-yl-1-triisopropylsilanyl-1H-indole | HCID 58974986 | — |
Reaction Steps
Following a method similar to 3-morpholin-4-yl-1-triisopropylsilanyl-1H-indole using 3-bromo-1-triisopropylsilanyl-1H-indole (0.70 g, 1.99 mmol), piperidine (0.26 g, 3.04 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (0.02 g, 0.05 mmol), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (0.05 g, 0.05 mmol) and 1N solution of lithium bis(trimethylsilyl)amide in THF (2.40 mL) to prepare the title compound. Purify by flash chromatography using 0 to 40% of EtOAc in hexanes to give the title compound (0.20 g, 29%): MS (ES) 357.1 (M+1)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07595339B2 |
| Source dataset | uspto-grants-2009_09 |
| ORD ID | ord-486366c11e7a4adf9adea29da3c07271 |
| Source note | uspto-grants-2009_09 |