HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Methylpiperazine → 3-(4-Methyl-piperazin-1-yl)-1-triisopropylsilanyl-1H-indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Methylpiperazine | HCID 53167 | — |
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Reactant | 3-Bromo-1-(triisopropylsilyl)indole | HCID 10991769 | — |
| Reactant | 3-Morpholin-4-yl-1-triisopropylsilanyl-1H-indole | HCID 58975176 | — |
| Catalyst | 2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl | HCID 2734217 | — |
| 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-(4-Methyl-piperazin-1-yl)-1-triisopropylsilanyl-1H-indole | HCID 58975109 | 32% |
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), 1-methyl-piperazine (0.30 g, 3.00 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). Purify by flash chromatography using 0 to 12% of MeOH in dichloromethane to give the title compound (0.23 g, 32%). MS (ES) 372.1 (M+1)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07595339B2 |
| Source dataset | uspto-grants-2009_09 |
| ORD ID | ord-6f34848a521c443fba5e741f1d6c53d9 |
| Source note | uspto-grants-2009_09 |