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

HRID 377661
ノート
印刷プレビュー

反応式

HRID 377661 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 8471TriethylamineHCID 66111Trimethylsilylacetylene2 回HCID 211881115-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethoxyphenyl)-4-iodopyrazole

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物
触媒
2 回
HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bc2c561ea9724ff38b1675faca0e4166
出典データセット
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06028096

反応ノート

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