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Triethylamine → 5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethoxyphenyl)-4-trimethylsilylethynylpyrazole

HRID 377661
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HRID 377661 반응식
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:9][C:8]=2[Cl:19])[N:5]=[C:4]([C:20]#[N:21])[C:3]=1I.[CH3:23][Si:24]([C:27]#[CH:28])([CH3:26])[CH3:25].C(N(CC)CC)C>CN(C)C=O.O.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>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:9][C:8]=2[Cl:19])[N:5]=[C:4]([C:20]#[N:21])[C:3]=1[C:28]#[C:27][Si:24]([CH3:26])([CH3:25])[CH3:23]
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참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 66111Trimethylsilylacetylene2회HCID 211881115-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethoxyphenyl)-4-iodopyrazole

생성물 1

HCID 211881085-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethoxyphenyl)-4-trimethylsilylethynylpyrazole

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물
촉매
2회
HCID 962Water용매
HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethoxyphenyl)-4-iodopyrazole (5.489 g) in dimethylformamide (4 ml) at room temperature was added trimethylsilylacetylene (3.35 ml), cuprous iodide (0.116 g), bis(triphenylphosphine)palladium(II) chloride (0.228 g) and triethylamine (1 ml). The mixture was heated at 60° C. for 2.5 hours. Trimethylsilylacetylene (1.675 ml), cuprous iodide (0.058 g) and bis(triphenylphosphine)palladium(II) chloride (0.114 g) were then added and stirring and heating was continued for a further period of one hour. The cooled reaction mixture was diluted with water and extracted with ether. The ether extract was dried (MgSO4) and evaporated to give the crude product which was purified by column chromatography on silica gel eluted with dichloromethane/hexane. Combination and evaporation of suitable fractions followed by recrystallisation of their residue from dichloromethane/hexane provided the title compound as a pale yellow solid, m.p. 151.5-152.1° C.

후처리

  1. temperatureheating
  2. customThe cooled reaction mixture
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. dry with materialwas dried (MgSO4)
  6. customevaporated
  7. customto give the crude product which
  8. customwas purified by column chromatography on silica gel
  9. washeluted with dichloromethane/hexane
  10. customCombination and evaporation of suitable fractions
  11. customfollowed by recrystallisation of their residue from dichloromethane/hexane

출처 및 근거

ORD 기록
ord-bc2c561ea9724ff38b1675faca0e4166
출처 데이터셋
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06028096

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