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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1623915Generated: October 30, 2026

2-Bromo-5-hydrazinylpyridine → (1aR,5aR)-2-(6-Bromopyridin-3-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic Acid Ethyl Ester

https://huagongshe.com/reaction/1623915

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-Bromo-5-hydrazinylpyridineHCID 52908344—
Reactantpotassium 2-ethoxy-2-oxo-((1R,5R)-2-oxobicyclo[3.1.0]hexan-3-ylidene)ethanolateHCID 68182523—
Product(1aR,5aR)-2-(6-Bromopyridin-3-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic Acid Ethyl EsterHCID 86669661—

Reaction Steps

The title compound was prepared in a manner similar to that described in Method C using potassium 2-ethoxy-2-oxo-1-((1R,5R)-2-oxobicyclo[3.1.0]hexan-3-ylidene)ethanolate and 2-bromo-5-hydrazinylpyridine. LCMS m/z=348.2 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 0.58 (td, J=4.8, 3.4 Hz, 1H), 1.30 (td, J=7.8, 5.1 Hz, 1H), 1.39 (t, J=7.2 Hz, 3H), 2.29-2.39 (m, 2H), 2.90 (d, J=16.6 Hz, 1H), 3.02 (dd, J=16.6, 6.2 Hz, 1H), 4.39 (q, J=7.1 Hz, 2H), 7.59 (d, J=8.2 Hz, 1H), 8.09 (dd, J=8.5, 2.9 Hz, 1H), 8.87 (d, J=2.8 Hz, 1H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08778950B2
Source datasetuspto-grants-2014_07
ORD IDord-94b634fd28794958ab21c951cdf9e538
Source noteuspto-grants-2014_07