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

HRID 471753

反応式

HRID 471753 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 8471Triethylamine溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-b169c76aac034637bdeed3ed70a44150
出典データセット
uspto-grants-2014_01
特許番号
US08633186B2

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