3-Chloro-1-(pyridine-3-yl)-1H-pyrazole-5-carboxylic acid hydrochloride → 3-(3-chloro-1H-pyrazol-1-yl)pyridine

HRID 57087

Reaktionsgleichung

Reaktionsgleichung von HRID 57087
Cl.[Cl:2][C:3]1[CH:7]=[C:6](C(O)=O)[N:5]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[N:4]=1>[Cu]=O.CN(C)C=O>[Cl:2][C:3]1[CH:7]=[CH:6][N:5]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[N:4]=1

Komponenten

4

Edukt 1

HCID 1180217823-Chloro-1-(pyridine-3-yl)-1H-pyrazole-5-carboxylic acid hydrochloride

Produkt 1

HCID 674995403-(3-chloro-1H-pyrazol-1-yl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14829Copper oxideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In step e of Scheme 4, 3-chloro-1-(pyridin-3-yl)-1H-pyrazole-5-carboxylic acid hydrochloride (6e) is decarboxylated in the presence of copper (II) oxide in polar solvents such as N,N-dimethylformamide at temperatures from about 80° C. to about 140° C. to yield 3-(3-chloro-1H-pyrazol-1-yl)pyridine (5b). It was surprisingly discovered that this decarboxylation only occurs in the presence of copper (II) oxide. Several known decarboxylation agents from the literature such as, for example, hydrochloric acid (See alternate synthetic route, Example 14), sulfuric acid, and palladium (II) trifluoroacetate/trifluoroacetic acid (See “CE-5”) did not yield the desired product.

Quellen und Nachweise

ORD-Eintrag
ord-c26f6f2537ea454e807c4477cfc5f432
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434712B2

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