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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1593510Generated: October 25, 2026

3-Nitropyridine → 6-Azaindole

https://huagongshe.com/reaction/1593510

Reaction equation

Participants

RoleNameHCIDCharge
Reactant3-NitropyridineHCID 137630—
ReactantHCID 178418507HCID 178418507—
SolventTetrahydrofuranHCID 8028—
Product6-AzaindoleHCID 9219—

Reaction Conditions

Temperature-20 °C

Reaction Steps

A solution of 3-nitropyridine in THF at −78° C. is treated with vinyl magnesium bromide (3 eq), stirred at −20° C. for 8 h and quenched with 20% ammonium chloride. The phases are separated and the aqueous phase is extracted with EtOAc. The organic phase and the combined extracts are mixed together, dried over MgSO4 and concentrated in vacuo. The resultant residue is chromatographed over silica gel to afford the title 6-azaindole.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07297705B2
Source datasetuspto-grants-2007_11
ORD IDord-92f7e06ab93f43a79f493fa076095c17
Source noteuspto-grants-2007_11