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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 490462Generated: October 31, 2026

Sodium Chloride → 5-Fluoro-1H-pyrrolo[2,3-b]pyridine

https://huagongshe.com/reaction/490462

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium ChlorideHCID 5234—
ReactantPotassium tert-butoxideHCID 23665647—
Reactant5-Fluoro-3-((trimethylsilyl)ethynyl)pyridin-2-amineHCID 59706849—
SolventN-methyl-2-pyrrolidoneHCID 13387—
Product5-Fluoro-1H-pyrrolo[2,3-b]pyridineHCID 2078446294.6%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07528147B2
Source datasetuspto-grants-2009_05
ORD IDord-d374acd764da456aa935bd759d884fb0
Source noteuspto-grants-2009_05