Trimethylsilylacetylene → 2-Amino-4'-(trimethylsilyl)ethinyl-biphenyl

HRID 1294454

反応式

HRID 1294454 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=1.[CH3:15][Si:16]([C:19]#[CH:20])([CH3:18])[CH3:17]>N1CCCCC1.O.[Cu]I.C1(P([Pd](Cl)(Cl)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:20]#[C:19][Si:16]([CH3:18])([CH3:17])[CH3:15])=[CH:10][CH:9]=1

参加物

7

反応物 2

HCID 66111TrimethylsilylacetyleneHCID 113686332-(4'-Bromophenyl)aniline

生成物 1

HCID 690159462-Amino-4'-(trimethylsilyl)ethinyl-biphenyl

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178479802HCID 178479802、化合物触媒HCID 962Water溶媒HCID 8082Piperidine溶媒

反応条件

温度
60 °C

実験手順

To 2.5 g 2-amino-4′-bromo-biphenyl (WO0264562) in piperidine (25 ml) under nitrogen were added in sequence CuI (0.1 g), bis(triphenylphosphino)palladium dichloride (0.35 g) and trimethylsilylacetylene (2.8 ml). The mixture was stirred for 22 hours at room temperature and for a further 26 hours at 60° C. After cooling the reaction mixture was diluted with water and extracted with ethylacetate. Then the organic phase was washed with water and dried over sodium sulfate. After evaporation of the solvents in vacuum the mixture was chromatographed on silica gel (hexane:ethylacetate 9:1) to yield 2- amino-4′-(trimethylsilyl)ethinyl-biphenyl (2 g) (Compound No.12.02).

後処理

  1. temperatureAfter cooling the reaction mixture
  2. extractionextracted with ethylacetate
  3. washThen the organic phase was washed with water
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation of the solvents in vacuum the mixture
  6. customwas chromatographed on silica gel (hexane:ethylacetate 9:1)

出典と根拠

ORDレコード
ord-ca7ef7cd598545db81b6d5c2f98e8557
出典データセット
uspto-grants-2007_07
特許番号
US07241721B2

関連ノート

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