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

HRID 57084

반응식

HRID 57084 반응식
[Cl:1][C:2]1[CH:6]=[C:5](C(O)=O)[N:4]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[N:3]=1>[Cu]=O.CN(C)C=O>[Cl:1][C:2]1[CH:6]=[CH:5][N:4]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[N:3]=1

참가 물질

4

반응물 1

HCID 917544803-chloro-1-(pyridin-3-yl)-1H-pyrazole-5-carboxylic acid

생성물 1

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

시약·촉매·용매 2

HCID 14829Copper oxide촉매HCID 6228Dimethylformamide용매

실험 절차

In step d of Scheme 2, 3-chloro-1-(pyridin-3-yl)-1H-pyrazole-5-carboxylic acid (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 (Pd(TFA)2/TFA) (See “CE-5”) did not yield the desired product.

출처 및 근거

ORD 기록
ord-1a23c4ccebed4846af0dbda241626759
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434712B2

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