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

HRID 1049234노트

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HRID 1049234 반응식
[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

참가 물질

8

반응물 4

HCID 178AcetamideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 90403315HCID 90403315, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl촉매HCID 312751,4-Dioxane용매

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온도
83 °C

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-7a540c3b0beb419386e69361b2edb6ea
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382228B2

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