Water → 3-(3-Nitropyridin-4-yl)cyclohex-2-enone

HRID 73568노트

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HRID 73568 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].O>O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O.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>[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

8

반응물 3

HCID 962WaterHCID 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 64%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매HCID 10340Sodium Carbonate용매HCID 312751,4-Dioxane용매

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온도
120 °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(PPh3)4 (0.05 equiv.). The reaction was heated in an oil bath to 120° C. for 30 min. (reaction can also be carried out in the microwave for 10 min at 120° C.). 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 to yield 3-(3-nitropyridin-4-yl)cyclohex-2-enone (64%, 2 steps). LC/MS=219 (M+H), LC=2.29 min.

후처리

  1. customreaction
  2. temperatureCooled to room temperature
  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

출처 및 근거

ORD 기록
ord-eea70daa6c434eceae314c3451c82ed7
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829193B2

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