Acetamide → N-(5-((2-chloropyridin-4-yl)oxy)-6-methylpyridin-2-yl)acetamide

HRID 1049234ノート

反応式

HRID 1049234 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH3:16])=[N:11][C:12](I)=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[C:17]([NH2:20])(=[O:19])[CH3:18].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>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:20][C:17](=[O:19])[CH3:18])=[N:11][C:10]=2[CH3:16])[CH:5]=[CH:4][N:3]=1

参加物

8

反応物 4

HCID 178AcetamideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 90403315HCID 90403315、化合物

生成物 1

HCID 90402585N-(5-((2-chloropyridin-4-yl)oxy)-6-methylpyridin-2-yl)acetamide収率 56%

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
83 °C

実験手順

A solution of 3-((2-chloropyridin-4-yl)oxy)-6-iodo-2-methylpyridine (8.5 g, 24.53 mmol) in dioxane (100 mL) was sparged with argon, treated with acetamide (5.07 g, 86 mmol), Cs2CO3 (11.99 g, 36.8 mmol), X-Phos (0.585 g, 1.226 mmol) and Pd2(dba)3 (1.123 g, 1.226 mmol) and heated at 83° C. for 16 h. The mixture was cooled to RT, treated with EtOAc, solids removed via filtration through diatomaceous earth, rinsed well with EtOAc, and the filtrate washed with H2O, then brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford N-(5-((2-chloropyridin-4-yl)oxy)-6-methylpyridin-2-yl)acetamide (3.8 g, 56%) as an off-white solid. MS (ESI) m/z: 278.0 (M+H+).

後処理

  1. temperatureThe mixture was cooled to RT
  2. customremoved via filtration through diatomaceous earth
  3. washrinsed well with EtOAc
  4. washthe filtrate washed with H2O
  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-7a540c3b0beb419386e69361b2edb6ea
出典データセット
uspto-grants-2016_07
特許番号
US09382228B2

反応ノート

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