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

HRID 1623915Notes

Reaction equation

HRID 1623915 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5](=[C:7]1[CH2:12][C@@H:11]2[C@@H:9]([CH2:10]2)[C:8]1=O)[O-])[CH3:2].[K+].[Br:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][NH2:24])=[CH:19][N:18]=1>>[CH2:1]([O:3][C:4]([C:5]1[C:7]2[CH2:12][C@H:11]3[CH2:10][C@H:9]3[C:8]=2[N:23]([C:20]2[CH:19]=[N:18][C:17]([Br:16])=[CH:22][CH:21]=2)[N:24]=1)=[O:14])[CH3:2]

Participants

3

Reactant 2

HCID 529083442-Bromo-5-hydrazinylpyridineHCID 68182523potassium 2-ethoxy-2-oxo-((1R,5R)-2-oxobicyclo[3.1.0]hexan-3-ylidene)ethanolate

Product 1

HCID 86669661(1aR,5aR)-2-(6-Bromopyridin-3-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic Acid Ethyl Ester

Procedure

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).

Sources & evidence

ORD record
ord-94b634fd28794958ab21c951cdf9e538
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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