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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 419280Generated: October 30, 2026

2,6-Dibromopyridine → 9-(6-Bromopyridin-2-yl)-3-azaspiro[5.5]undec-8-ene

https://huagongshe.com/reaction/419280

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2,6-DibromopyridineHCID 12274—
Reactanttert-Butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylateHCID 51072194—
ReactantButyllithiumHCID 178418339—
SolventDichloromethaneHCID 6344—
Product9-(6-Bromopyridin-2-yl)-3-azaspiro[5.5]undec-8-eneHCID 16006433—

Reaction Conditions

Temperature-78 °C

Reaction Steps

Was prepared according to method A with the following variation: n-BuLi (1.6 M in hexanes (1.93 mL, 4.82 mmol)) was added drop-wise to a solution of 2,6-dibromopyridine (1.06 g, 4.48 mmol) in dichloromethane (25 mL). The reaction was stirred −78° C. for 30 min. 9-Oxo-3-aza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester (300 mg, 1.12 mmol) in dichloromethane (5 mL) was added drop-wise and the mixture was stirred at −78° C. for 1 h. White solid. Mp. 161.3-162.8° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08093388B2
Source datasetuspto-grants-2012_01
ORD IDord-ddc3ebe233a642649bd7903e5dc13537
Source noteuspto-grants-2012_01