Dimethylformamide → HCID 178474487, 화합물

HRID 588596노트

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HRID 588596 반응식
C([N:4]1[C:8]([NH:9][C:10](=[O:12])[CH3:11])=[C:7](I)[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:5]1)(=O)C.[C:20]1([C:26]#[CH:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C.CN(C=O)C>C(OCC)(=O)C.O.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:14]1([C:6]2[C:7]([C:27]#[C:26][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:8]([NH:9][C:10](=[O:12])[CH3:11])[NH:4][N:5]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

참가 물질

9

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 86717296N-(2-acetyl-4-iodo-5-phenyl-pyrazol-3-yl)acetamide

생성물 1

HCID 178474487HCID 178474487, 화합물수율 48%

시약·촉매·용매 4

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

Nitrogen was bubbled through a mixture of N-(2-acetyl-4-iodo-5-phenyl-pyrazol-3-yl)acetamide (31.87 g, 86.4 mmol), phenyl acetylene (17.6 g, 173 mmol), triethylamine (200 mL) and DMF (100 mL) for 15 min. Copper iodide (1.64 g, 8.6 mmol) and bis(triphenylphosphine)palladium(II) dichloride (3.0 g, 4.3 mmol) were added and the reaction mixture was stirred at 90° C. under nitrogen for 3 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and water. The organic phase was washed with water and brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (silica gel, iso-hexanes/ethyl acetate 5:1 to 1:1) yielding the title compound as a solid (12.5 g).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel, iso-hexanes/ethyl acetate 5:1 to 1:1)

출처 및 근거

ORD 기록
ord-f0f3fb93dde043c49860acb4b64811e9
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227976B2

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