HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Chloride → 5-Fluoro-1H-pyrrolo[2,3-b]pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Chloride | HCID 5234 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | 5-Fluoro-3-((trimethylsilyl)ethynyl)pyridin-2-amine | HCID 59706849 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | 5-Fluoro-1H-pyrrolo[2,3-b]pyridine | HCID 20784462 | 94.6% |
Reaction Steps
A mixture of 3.8 g of 5-fluoro-3-trimethylsilanylethynylpyridin-2-ylamine and 3.4 g of potassium tert-butoxide in 100 ml of 1-methylpyrrolidin-2-one is brought to around 130° C. for approximately 4 hours. After returning to a temperature in the region of 20° C., the mixture is run into 1000 ml of a saturated aqueous sodium chloride solution and extracted with five times 250 ml of diethyl ether. The organic phases are combined, washed with five times 100 ml of a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated to dryness under reduced pressure (13 kPa). 2.35 g of 5-fluoro-1H-pyrrolo[2,3-b]pyridine are obtained in the form of a solid, the characteristics of which are as follows:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07528147B2 |
| Source dataset | uspto-grants-2009_05 |
| ORD ID | ord-d374acd764da456aa935bd759d884fb0 |
| Source note | uspto-grants-2009_05 |