HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Chloride → 5-Bromo-N-cyclohexyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Chloride | HCID 5234 | — |
| Reactant | Cyclohexylamine | HCID 7965 | — |
| Reactant | 5-Bromo-4-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo(2,3-b)pyridine | HCID 57537666 | — |
| Solvent | Ethylene Glycol | HCID 174 | — |
| Product | 5-Bromo-N-cyclohexyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-amine | HCID 71258476 | 80% |
Reaction Steps
5-Bromo-4-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine (150 mg, 0.415 mmol) and cyclohexylamine (1 mL, 9 mmol) in ethylene glycol (1 mL) were stirred at 200° C. for 2 hour under microwave irradiation. The reaction mixture was allowed to cool to room temperature and, after addition of saturated aqueous sodium chloride, extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1 (v/v)) to give the title compound as an orange oil (141 mg, yield 80%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09216999B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-43b72dc9b30049ae99a689a78404bd77 |
| Source note | uspto-grants-2015_12 |