Water → 5-Methyl-3-(3-nitro-4-pyridinyl)-2-cyclohexen-1-one

HRID 73575노트

반응식

HRID 73575 반응식
[CH3:1][CH:2]1[CH2:7][C:6](=[O:8])[CH:5]=[C:4](B2OC(C)(C)C(C)(C)O2)[CH2:3]1.Cl[C:19]1[CH:24]=[CH:23][N:22]=[CH:21][C:20]=1[N+:25]([O-:27])=[O:26].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>[CH3:1][CH:2]1[CH2:7][C:6](=[O:8])[CH:5]=[C:4]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][C:20]=2[N+:25]([O-:27])=[O:26])[CH2:3]1

참가 물질

8

반응물 3

HCID 962WaterHCID 27357814-Chloro-3-nitropyridineHCID 592265515-Methyl-2-cyclohexene-1-one-3-boronic acid pinacol ester

생성물 1

HCID 592265435-Methyl-3-(3-nitro-4-pyridinyl)-2-cyclohexen-1-one

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 5-methyl-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 2 h. (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 5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enone. LC/MS=233.2 (M+H); Rt=0.69 min, LC=2.70 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-bbce25c38c314dc5b915bb28fc586f45
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829193B2

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