Trimethyl-2-propynylsilane → 2-Amino-6-(3-(trimethylsilyl)prop-1-ynyl)benzonitrile

HRID 471753노트

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HRID 471753 반응식
[CH3:1][Si:2]([CH3:7])([CH3:6])[CH2:3][C:4]#[CH:5].[NH2:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13](Br)[C:10]=1[C:11]#[N:12]>C(N(CC)CC)C.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13]([C:5]#[C:4][CH2:3][Si:2]([CH3:7])([CH3:6])[CH3:1])[C:10]=1[C:11]#[N:12]

참가 물질

6

반응물 2

HCID 83378Trimethyl-2-propynylsilaneHCID 98130382-Amino-6-bromobenzonitrile

생성물 1

HCID 674002162-Amino-6-(3-(trimethylsilyl)prop-1-ynyl)benzonitrile수율 125.2%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8471Triethylamine용매

실험 절차

To a stirred solution of trimethyl(prop-2-ynyl)silane (1.12 g, 10 mmol), 2-amino-6-bromobenzonitrile (Klaubert, D. H.; Sellstedt, J. H.; Guinosso, C. J.; Capetola, R. J.; Bell, S. C. J. Med. Chem. 1981, 24, 742) (1.0 g, 5 mmol), CuI (0.01 equiv.) in triethylamine (50 mL) was added Pd(PPh3)4 (0.1 equiv.) at room temperature under nitrogen. The reaction mixture was then refluxed under nitrogen overnight. The solvent was evaporated, and the residue was titrated with EtOAc/water. The organic layer was separated, were washed with brine, and dried over Na2SO4. After evaporation of the solvent, the residue was purified by chromatography on silica gel eluting with 15% EtOAc in hexanes to give the title compound (1.43 g, 63%) as a as a liquid. MS 229 (MH+).

후처리

  1. temperatureThe reaction mixture was then refluxed under nitrogen overnight
  2. customThe solvent was evaporated
  3. customThe organic layer was separated
  4. washwere washed with brine
  5. dry with materialdried over Na2SO4
  6. customAfter evaporation of the solvent
  7. customthe residue was purified by chromatography on silica gel eluting with 15% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-b169c76aac034637bdeed3ed70a44150
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633186B2

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