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

HRID 2383343ノート

反応式

HRID 2383343 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2c093670350a4fb7b86a3550d6ea04c7
出典データセット
uspto-grants-2012_09
特許番号
US08263622B2

反応ノート

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