Nitrogen → 4-Bromo-1-phenyl-1H-pyrazole

HRID 40377

반응식

HRID 40377 반응식
[Br:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.I[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+].N#N>CCOC(C)=O.[Cu](I)I.O1CCOCC1>[Br:1][C:2]1[CH:3]=[N:4][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=1

참가 물질

9

반응물 5

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 163754-BromopyrazoleHCID 438061,2-Diaminocyclohexane, trans-

생성물 1

HCID 7868114-Bromo-1-phenyl-1H-pyrazole

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

A sealable tube was charged with 4-bromopyrazole (4.000 g, 27.2 mmol), 1-iodobenzene (3.64 ml, 32.7 mmol), (+/−)-trans-1,2-diaminocyclohexane (0.654 ml, 5.44 mmol), Copper iodide (I) (0.518 g, 2.72 mmol), potassium carbonate (8.28 g, 59.9 mmol) and 13 mL dioxane added. The mixture was blanketed with N2, the vessel sealed and heated to 100 C for 16 h. The mixture was allowed to cool to rt, diluted with EtOAc, washed with water, and an emullsion formed. The organic layer separated and the aqueous emulsion mixture was filter through a pad of celite and rinsed with EtOAc, and sat. NaHCO3. The combined organig layers were dried over Na2SO4, filtered and evaporate. The mixture was purified via flash chromatography using a 0% to 100% CH2Cl2 in hexanes gradient. The title compound was collected as a yellow solid (3.18 g)

후처리

  1. additionadded
  2. customthe vessel sealed
  3. temperatureheated to 100 C for 16 h
  4. washwashed with water
  5. customan emullsion formed
  6. customThe organic layer separated
  7. filtrationthe aqueous emulsion mixture was filter through a pad of celite
  8. washrinsed with EtOAc, and sat. NaHCO3
  9. dry with materialThe combined organig layers were dried over Na2SO4
  10. filtrationfiltered
  11. customevaporate
  12. customThe mixture was purified via flash chromatography
  13. customThe title compound was collected as a yellow solid (3.18 g)

출처 및 근거

ORD 기록
ord-5aeb37f62849404ab729720b2c74811c
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524900B2

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