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

HRID 1971419노트

반응식

HRID 1971419 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 111,2-Dichloroethane용매2회

반응 조건

온도
70 °C

실험 절차

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. 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).

후처리

  1. stirringThe resulting dark-green mixture is stirred at 70° C. for 24 h
  2. customThe 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%)

출처 및 근거

ORD 기록
ord-c0d7c152160145f786da9505c86366c8
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431584B2

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