3-Chloro-2-pyrazine-carboxylic acid → Ethyl 3-chloro-beta-oxo-2-pyrazinepropanoate

Reaction equation

[Cl:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][N:7]=1.C(O)(=O)CC(O)=O.C([K])C.[CH2:21]([O:23][C:24](=[O:35])[CH2:25]C(C1C(F)=CC=CN=1)=O)[CH3:22]>>[CH2:21]([O:23][C:24](=[O:35])[CH2:25][C:8]([C:3]1[C:2]([Cl:1])=[N:7][CH:6]=[CH:5][N:4]=1)=[O:10])[CH3:22]

Participants

Reactant 3

HCID 15019003-Chloro-2-pyrazine-carboxylic acid

HCID 59864622Ethyl 3-(3-fluoropyridin-2-yl)-3-oxopropanoate

HCID 178461627HCID 178461627, compound

Product 1

HCID 86725436Ethyl 3-chloro-beta-oxo-2-pyrazinepropanoateYield 39.54%

Procedure

3-(3-Chloro-pyrazin-2-yl)-3-oxo-propionic acid ethyl ester (12) (2 g, 39.54%) was synthesized as a yellow liquid from 3.5 g of 3-chloro-pyrazine-2-carboxylic acid (11) and 5.64 g of ethyl potassium malonate (2) following the procedure described for 3-(3-fluoro-pyridin-2-yl)-3-oxo-propionic acid ethyl ester (3).

Sources & evidence

ORD record: ord-d1930d1553cb47b5a8ad72cb180a3cb1
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199987B2

Reaction notes

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