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

HRID 1523412ノート

反応式

HRID 1523412 の反応式
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]

参加物

7

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418807HCID 178418807、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 10340Sodium Carbonate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-74bb4c80fe414fa78fff8fe595fb1195
出典データセット
uspto-grants-2015_07
特許番号
US09079889B2

反応ノート

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