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

HRID 1294454

반응식

HRID 1294454 반응식
[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

참가 물질

7

반응물 2

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

생성물 1

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

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178479802HCID 178479802, 화합물촉매HCID 962Water용매HCID 8082Piperidine용매

반응 조건

온도
60 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ca7ef7cd598545db81b6d5c2f98e8557
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07241721B2

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