Ethyl Acetate → Ethyl 1-(6-phenylpyridin-3-yl)cyclopropanecarboxylate

HRID 557819노트

반응식

HRID 557819 반응식
C(=O)([O-])[O-].[Na+].[Na+].Cl[C:8]1[N:13]=[CH:12][C:11]([C:14]2([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(OCC)(=O)C>O.C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:22]1([C:8]2[N:13]=[CH:12][C:11]([C:14]3([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH2:15]3)=[CH:10][CH:9]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

9

반응물 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 86602273Ethyl 1-(6-chloropyridin-3-yl)cyclopropanecarboxylate

생성물 1

HCID 66661635Ethyl 1-(6-phenylpyridin-3-yl)cyclopropanecarboxylate

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 1140Toluene용매

실험 절차

Sodium carbonate (42.4 mg, 0.400 mmol) in water (0.20 mL) was added to a mixture of ethyl 1-(6-chloropyridin-3-yl)cyclopropanecarboxylate (45.1 mg, 0.200 mmol), Phenylboronic acid (24.4 mg, 0.200 mmol) and tetrakis(triphenylphosphine)palladium(0) (7.15 mg) in toluene (200.0 μL) and ethanol (100.0 μL). The resulting mixture was irradiated by microwave at 120° C. for 15 minutes. Ethyl acetate (5 mL) was then added to the mixture. The resulting mixture was washed with water followed by brine. The organic layer was dried over Na2SO4, then filtered, and then concentrated under reduced pressure. The residue was purified by flash chromatography with ethyl acetate/hexane to give ethyl 1-(6-phenylpyridin-3-yl)cyclopropanecarboxylate.

후처리

  1. customThe resulting mixture was irradiated by microwave at 120° C. for 15 minutes
  2. washThe resulting mixture was washed with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography with ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-32961ba308614a839d8e3bb0a38a77c9
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058288B2

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