Ethyl Acetate → 3-(3-chloro-1H-pyrazol-1-yl)pyridine

HRID 57091

반응식

HRID 57091 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.C(OCC)(=O)C>CN(C)C=O.[OH-].[NH4+].O.[Cu]=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

7

반응물 2

HCID 8857Ethyl AcetateHCID 1180217823-Chloro-1-(pyridine-3-yl)-1H-pyrazole-5-carboxylic acid hydrochloride

생성물 1

HCID 674995403-(3-chloro-1H-pyrazol-1-yl)pyridine수율 73.4%

시약·촉매·용매 4

HCID 14829Copper oxide촉매2회HCID 962Water용매HCID 6228Dimethylformamide용매HCID 14923Ammonium Hydroxide용매

반응 조건

온도
120 °C

실험 절차

3-Chloro-1-(pyridin-3-yl)-1H-pyrazole-5-carboxylic acid hydrochloride (1.00 g, 3.65 mmol) was stirred in N,N-dimethylformamide (10 mL). Copper(II) oxide (58.0 mg, 0.730 mmol) was added and the reaction was heated at 120° C. for 16 hours, at which point the reaction was ˜20% complete. Additional copper(II) oxide (112 mg, 1.46 mmol) was added and the reaction was stirred for 5 hours, at which point the reaction was complete by thin layer chromatography (TLC) [Eluent: ethyl acetate]. The mixture was diluted with ammonium hydroxide (NH4OH) and water and extracted with ethyl acetate. The organic layer was washed with 15% lithium chloride and concentrated to provide an orange solid. The residue was purified by flash column chromatography using ethyl acetate as eluent and the pure fractions were concentrated to afford the desired product as a white solid (481 mg, 69.7%). The spectral characterization was in agreement with the product prepared previously.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 15% lithium chloride
  3. concentrationconcentrated
  4. customto provide an orange solid
  5. customThe residue was purified by flash column chromatography
  6. concentrationthe pure fractions were concentrated

출처 및 근거

ORD 기록
ord-e057a9d09fff4e41a0af34e569f9968e
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434712B2

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