2,2'-Bipyridine → 1,5-Dicyclopropyl-3-(2,5-dimethyl-pyrrol-1-yl)-1H-pyrazole

HRID 45153

反応式

HRID 45153 の反応式
N1C=CC=CC=1[C:7]1[CH:12]=[CH:11]C=CN=1.[CH:13]1([C:16]2[NH:20][N:19]=[C:18]([N:21]3[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]3[CH3:27])[CH:17]=2)[CH2:15][CH2:14]1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH:11]1([N:20]2[C:16]([CH:13]3[CH2:15][CH2:14]3)=[CH:17][C:18]([N:21]3[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]3[CH3:27])=[N:19]2)[CH2:12][CH2:7]1

参加物

6

反応物 3

HCID 14742,2'-BipyridineHCID 10340Sodium CarbonateHCID 593946605-Cyclopropyl-3-(2,5-dimethyl-pyrrol-1-yl)-1H-pyrazole

生成物 1

HCID 593947901,5-Dicyclopropyl-3-(2,5-dimethyl-pyrrol-1-yl)-1H-pyrazole収率 104.2%

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 111,2-Dichloroethane溶媒2 回

反応条件

温度
70 °C

実験手順

A suspension of copper (II) acetate (0.902 g, 4.97 mmol) and 2,2′-bipyridine (0.776 g, 4.97 mmol) in DCE (20 mL) is stirred at 70° C. for 15 min, then transferred to a suspension of cyclopropyl trifluoroborate potassium salt (1.47 g, 9.94 mmol) and 5-Cyclopropyl-3-(2,5-dimethyl-pyrrol-1-yl)-1H-pyrazole (1 g, 4.97 mmol), and sodium carbonate (1.053 g, 9.94 mmol) in DCE (40 mL). The resulting dark-green mixture is stirred at 70° C. for 24 h. T The reaction mixture is partitioned between EtOAc and 1N HCl. The aqueous layer is extracted with EtOAc. The combined organic layers are washed with brine, dried (Na2SO4) and concentrated. The residue (1.64 g) is purified by ISCO (EtOAc-heptane 0-30%) to provide the desired product (1.25 g) as a colorless oil. MS (ESI) m/z 242.3 (M+1).

後処理

  1. stirringThe resulting dark-green mixture is stirred at 70° C. for 24 h
  2. customT The reaction mixture is partitioned between EtOAc and 1N HCl
  3. extractionThe aqueous layer is extracted with EtOAc
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue (1.64 g) is purified by ISCO (EtOAc-heptane 0-30%)

出典と根拠

ORDレコード
ord-d2d5fd8e56d141a08b39d578e86e99af
出典データセット
uspto-grants-2013_09
特許番号
US08541432B2

関連ノート

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