3-Bromoaniline → 3-(1H-Pyrazol-3-yl)aniline

HRID 240168

반응식

HRID 240168 반응식
[NH:1]1[C:5](B(O)O)=[CH:4][CH:3]=[N:2]1.Br[C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][CH:16]=1)[NH2:13].[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>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]>[N:2]1[NH:1][C:5]([C:10]2[CH:11]=[C:12]([NH2:13])[CH:14]=[CH:15][CH:16]=2)=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 115623-BromoanilineHCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 112519791H-Pyrazole-5-boronic acid

생성물 1

HCID 27353983-(1H-Pyrazol-3-yl)aniline수율 20%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

실험 절차

1H-pyrazole-5-boronic acid (0.072 g, 0.639 mmol) and 3-bromoaniline (0.063 mL, 0.581 mmol) were combined in dioxane (2 mL) in a flame-dried, round-bottom flask. K3PO4 (1.27M, 0.778 mL, 0.99 mmol), PCy3 (0.004 g, 0.014 mmol), and Pd2(dba)3 (0.005 g, 0.006 mmol) were added to the stirred solution. The reaction was refluxed overnight under argon flow, and subsequently cooled to room temperature. The solvent was removed under vacuum and the resulting residue was resuspended in CH2Cl2. The organic phase was dried over MgSO4, filtered, and concentrated under vacuum. The crude product was purified by flash silica column chromatography (70-100% EtOAc/hexanes). The purification was monitored by TLC. The solvent was removed under vacuum from fractions containing product, resulting in 0.018 g in 20% yield.

후처리

  1. temperatureThe reaction was refluxed overnight under argon flow
  2. customThe solvent was removed under vacuum
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified by flash silica column chromatography (70-100% EtOAc/hexanes)
  7. customThe purification
  8. customThe solvent was removed under vacuum from fractions
  9. additioncontaining product
  10. customresulting in 0.018 g in 20% yield

출처 및 근거

ORD 기록
ord-95666a464a764a6eb78e00dfa43597f5
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642788B2

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