Potassium Carbonate → 1-(4-cyanonaphthalene-2-yl)-1H-pyrazole-3-carboxylic acid ethyl ester

HRID 2383343노트

반응식

HRID 2383343 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[CH:9][NH:8][N:7]=1)=[O:5])[CH3:2].Br[C:12]1[CH:13]=[C:14]([C:22]#[N:23])[C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2.CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.[Cu](I)I.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[CH:9][N:8]([C:12]2[CH:13]=[C:14]([C:22]#[N:23])[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:21]=2)[N:7]=1)=[O:5])[CH3:2]

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 534856703-Bromonaphthalene-1-carbonitrileHCID 178469268HCID 178469268, 화합물

생성물 1

HCID 673092091-(4-cyanonaphthalene-2-yl)-1H-pyrazole-3-carboxylic acid ethyl ester수율 19.2%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
90 °C

실험 절차

A suspension of 1H-pyrazole-3-carboxylic acid ethyl ester (0.1 g), 3-bromonaphthalene-1-carbonitrile (0.17 g), copper iodide (0.0068 g), (1R,2R)-(−)-N, N′-dimethylcyclohexane-1,2-diamine (0.010 g) and potassium carbonate (0.21 g) in toluene (3 mL) was stirred at 90° C. overnight. After cooling to room temperature, ethyl acetate was added to the reaction mixture. The resulting mixture was filtered through a Celite pad. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=100/0-66/34) to give 1-(4-cyanonaphthalene-2-yl)-1H-pyrazole-3-carboxylic acid ethyl ester (0.040 g). To a solution of this compound (0.040 g) in a mixed solvent of tetrahydrofuran (0.2 mL), ethanol (0.08 mL) and water (0.08 mL) was added lithium hydroxide monohydrate (0.017 g), and the mixture was stirred at room temperature overnight. To the reaction mixture was added 2 mol/L hydrochloric acid (0.35 mL). The precipitated solid was collected by filtration, washed with water and n-hexane, and dried under reduced pressure to give the title compound (0.026 g).

후처리

  1. temperatureAfter cooling to room temperature
  2. filtrationThe resulting mixture was filtered through a Celite pad
  3. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=100/0-66/34)

출처 및 근거

ORD 기록
ord-2c093670350a4fb7b86a3550d6ea04c7
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263622B2

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