HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → 5-Chloro-4-fluoro-1H-pyrrolo[2,3-B]pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | 5-Chloro-4-fluoro-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine | HCID 60205273 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 5-Chloro-4-fluoro-1H-pyrrolo[2,3-B]pyridine | HCID 53412953 | 89.2% |
Reaction Steps
5-Chloro-4-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (3.0 g, 9.2 mmol) in THF (15 mL) at 0° C. was treated dropwise with TBAF (10.1 mL, 10.1 mmol). After 30 minutes, the reaction was quenched with saturated aqueous NaHCO3 and extracted into CH2Cl2. The combined organic fractions were dried (MgSO4), filtered, and concentrated in vacuo. The crude was purified by flash chromatography on silica gel using 1.2% MeOH:CH2Cl2 to provide 5-chloro-4-fluoro-1H-pyrrolo[2,3-b]pyridine (1.4 g, 89% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08178131B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-fea28c40b7694f73b67d6b1692c8d5e6 |
| Source note | uspto-grants-2012_05 |