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

HRID 626549
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HRID 626549 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.[C:19]([NH2:24])(=[O:23])[CH:20]([CH3:22])[CH3:21].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:19](=[O:23])[CH:20]([CH3:22])[CH3:21])[CH:7]=2)=[CH:14][CH:13]=[C:12]([N+:15]([O-:17])=[O:16])[N:11]=1
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참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 68424IsobutyramideHCID 904036213-((2-Chloropyridin-4-yl)oxy)-2-methyl-6-nitropyridine

생성물 1

HCID 90410828N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)isobutyramide수율 92.4%

시약·촉매·용매 3

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

반응 조건

온도
90 °C

실험 절차

A mixture of Example A3 (0.50 g, 1.882 mmol), isobutyramide (0.656 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. for 20 h. 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)isobutyramide (550 mg, 92%). MS (ESI) m/z: 317.1 (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-a4c1143fab234dc696b3160ce5158451
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09309224B2

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