Sodium Carbonate → 3-(3-Nitropyridin-4-yl)cyclohex-2-enone

HRID 924408노트

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HRID 924408 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].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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

6

반응물 3

HCID 10340Sodium CarbonateHCID 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 87%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 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-en-1-one (6.0 g, 27 mmol) and 4-chloro-3-nitropyridine (2.4 g, 15 mmol) in 1,4-dioxane (60 mL), 2.0 N aq. Na2CO3 (12 mL, 24 mmol) and tetrakis(triphenylphosphine)palladium(0) (1.8 g, 1.5 mmol) were added. The reaction mixture was heated at 120° C. for 1 h. The reaction mixture was filtered through diatomaceous earth, which was washed with EtOAc. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluting with 10-100% EtOAc in hexanes) to give the sub-title compound as a brown solid (1.97 g, 87%). LCMS calc. for C11H11N2O3 (M+H)+: m/z=219.1. Found: 219.0.

후처리

  1. filtrationThe reaction mixture was filtered through diatomaceous earth, which
  2. washwas washed with EtOAc
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluting with 10-100% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-4416c30fbbca45078ff7baece52e298a
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278950B2

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