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

HRID 471753Notes

Reaction equation

HRID 471753 reaction equation
[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]

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-b169c76aac034637bdeed3ed70a44150
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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