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

HRID 57087

반응식

HRID 57087 반응식
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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 14829Copper oxide촉매HCID 6228Dimethylformamide용매

실험 절차

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.

출처 및 근거

ORD 기록
ord-c26f6f2537ea454e807c4477cfc5f432
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434712B2

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