Cesium carbonate → N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide

HRID 626500노트

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HRID 626500 반응식
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH3:18])=[N:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[CH:19]1([C:22]([NH2:24])=[O:23])[CH2:21][CH2:20]1.C([O-])([O-])=O.[Cs+].[Cs+]>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>[CH3:18][C:10]1[C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:24][C:22]([CH:19]3[CH2:21][CH2:20]3)=[O:23])[CH:7]=2)=[CH:14][CH:13]=[C:12]([N+:15]([O-:17])=[O:16])[N:11]=1

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 80376CyclopropanecarboxamideHCID 904036213-((2-Chloropyridin-4-yl)oxy)-2-methyl-6-nitropyridine

생성물 1

HCID 90410595N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide수율 85%

시약·촉매·용매 3

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

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온도
90 °C

실험 절차

A mixture of Example A3 (0.50 g, 1.882 mmol), cyclopropanecarboxamide (0.641 g, 7.53 mmol), Cs2CO3 (0.920 g, 2.82 mmol), and X-phos (0.045 g, 0.094 mmol) in dioxane (10 mL) was sparged with Ar, treated with Pd2(dba)3 (0.086 g, 0.094 mmol), sparged again with Ar and heated at 90° C. overnight. The mixture was cooled to RT, treated with EtOAc and the solids removed via filtration. The filtrate was washed with brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/DCM) to afford N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide (500 mg, 85%). MS (ESI) m/z: 315.1 (M+H+).

후처리

  1. customsparged again with Ar
  2. temperatureThe mixture was cooled to RT
  3. additiontreated with EtOAc
  4. customthe solids removed via filtration
  5. washThe filtrate was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness
  8. custompurified via silica gel chromatography (EtOAc/DCM)

출처 및 근거

ORD 기록
ord-6457e0a0098e42dd84248a76174b4ece
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309224B2

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