Acetamide → N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide

HRID 626496

反応式

HRID 626496 の反応式
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[N:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[C:18]([NH2:21])(=[O:20])[CH3:19].C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>[N+:15]([C:12]1[N:11]=[CH:10][C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:21][C:18](=[O:20])[CH3:19])[CH:7]=2)=[CH:14][CH:13]=1)([O-:17])=[O:16]

参加物

8

反応物 4

HCID 178AcetamideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 593227792-Chloro-4-((6-nitropyridin-3-yl)oxy)pyridine

生成物 1

HCID 90409856N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide収率 68%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

A degassed solution of Example A1 (2.0 g, 7.95 mmol) in dioxane (30 mL) added treated with acetamide (1.878 g, 31.8 mmol), Cs2CO3 (2.59 g, 7.95 mmol), X-Phos (0.189 g, 0.397 mmol), and Pd2(dba)3 (0.364 g, 0.397 mmol) and heated at 80° C. for 16 h. The mixture was cooled to RT, treated with EtOAc, the solids removed via filtration through diatomaceous earth and rinsed well with EtOAc. The filtrate was washed with water, then brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide (1.48 g, 68%). MS (ESI) m/z: 275.1 (M+H+).

後処理

  1. temperatureThe mixture was cooled to RT
  2. customthe solids removed via filtration through diatomaceous earth
  3. washrinsed well with EtOAc
  4. washThe filtrate was washed with water
  5. dry with materialbrine, dried over Na2SO4
  6. concentrationconcentrated to dryness
  7. custompurified via silica gel chromatography (EtOAc/Hex)

出典と根拠

ORDレコード
ord-b3c4a19b1b1e40a3bb8d496342721504
出典データセット
uspto-grants-2016_04
特許番号
US09309224B2

関連ノート

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