HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 2-(6-chloro-5-methyl-2-(triethylsilyl)-1H-indol-3-yl)ethanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Lithium Chloride | HCID 433294 | — |
| Reactant | 4-(Triethylsilyl)-3-butyn-1-ol | HCID 2760694 | — |
| Reactant | 5-Chloro-2-iodo-4-methylaniline | HCID 58475405 | — |
| Catalyst | Palladium Chloride | HCID 24290 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-(6-chloro-5-methyl-2-(triethylsilyl)-1H-indol-3-yl)ethanol | HCID 66832034 | 79.2% |
Reaction Steps
2-(6-chloro-5-methyl-2-(triethylsilyl)-1H-indol-3-yl)ethanol was prepared according to method D Step II with 5-chloro-2-iodo-4-methylaniline (1.50 g; 5.61 mmol), 4-(triethylsilyl)but-3-yn-1-ol (2.36 mL; 11.22 mmol), Bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.229 g; 0.280 mmol), lithium chloride (0.237 g; 5.61 mmol) and sodium carbonate (1.19 g; 11.22 mmol) in DMF (14 mL). The crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to afford 1.44 g (79%) of 2-(6-chloro-5-methyl-2-(triethylsilyl)-1H-indol-3-yl)ethanol as a brown oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09284271B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-d76202676c184f7c94bd5e31a07d2437 |
| Source note | uspto-grants-2016_03 |