4-Chloro-3-nitropyridine → 3-(3-Nitropyridin-4-yl)cyclohex-2-enone

HRID 1523412노트

반응식

HRID 1523412 반응식
CC1(C)C(C)(C)OB([C:9]2[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[CH:10]=2)O1.Cl[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25]>O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[N+:24]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:18]=1[C:9]1[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[CH:10]=1)([O-:26])=[O:25]

참가 물질

7

반응물 2

HCID 27357814-Chloro-3-nitropyridineHCID 574964223-(Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-2-en-1-one

생성물 1

HCID 592265443-(3-Nitropyridin-4-yl)cyclohex-2-enone수율 55%

시약·촉매·용매 4

HCID 178418807HCID 178418807, 화합물촉매HCID 8857Ethyl Acetate용매HCID 10340Sodium Carbonate용매HCID 312751,4-Dioxane용매

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온도
110 °C

실험 절차

To a solution of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-2-enone (1.0 equiv.) in degassed dioxane and 2M Na2CO3 was added 4-chloro-3-nitropyridine (1.2 equiv.) and Pd(dppf)Cl2-DCM (0.05 equiv.). The reaction was heated in an oil bath to 110° C. for 2 hours. Cooled to room temperature, then diluted with EtOAc, added H2O— dark solution, lots of emulsions. Filtered to get rid of the solids, then extracted the organic phase, dried with Na2SO4, and concentrated. The crude was purified via silica gel chromatography eluting with ethyl acetate and hexanes (1:1) to yield 3-(3-nitropyridin-4-yl)cyclohex-2-enone (55%, 2 steps). LC/MS=219 (M+H), LC=2.294 min.

후처리

  1. temperatureCooled to room temperature
  2. additionadded H2O— dark solution, lots of emulsions
  3. filtrationFiltered
  4. customto get rid of the solids
  5. extractionextracted the organic phase
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated
  8. customThe crude was purified via silica gel chromatography
  9. washeluting with ethyl acetate and hexanes (1:1)

출처 및 근거

ORD 기록
ord-74bb4c80fe414fa78fff8fe595fb1195
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079889B2

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