Triethylamine → 4-Amino-5-ethynyl-2-(trifluoromethyl)benzenecarbonitrile

HRID 415967Notes

Reaction equation

HRID 415967 reaction equation
[NH2:1][C:2]1[C:9](I)=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.[CH2:15](N(CC)CC)[CH3:16].C([Si](C)(C)C)#C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[C:9]([C:15]#[CH:16])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 2724141Tetrabutylammonium FluorideHCID 250673774-Amino-5-iodo-2-(trifluoromethyl)benzonitrile

Product 1

HCID 665451724-Amino-5-ethynyl-2-(trifluoromethyl)benzenecarbonitrile

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Amino-5-iodo-2-trifluoromethyl-benzonitrile (936 mg, 3.0 mmol), CuI (I) (57 mg, 0.3 mmol), PdCl2(PPh3)2 (105.3 mg, 0.15 mmol), triethylamine (1.01 g, 10 mmol) and ethynyl-trimethyl-silane (450 mg, 4.5 mmol) were mixed in THF (30 ml). The reaction mixture was stirred at room temperature overnight. Tetrabutylammonium fluoride (1.0 M in THF, 3.0 ml, 3.0 mmol) was added to the reaction mixture, which was then stirred at room temperature for 20 mins. The reaction mixture was quenched by addition of H2O and extracted with ethyl acetate. The organic layers were combined and washed with brine, dried over Na2SO4 and concentrated to yield crude product 4-amino-5-ethynyl-2-trifluoromethyl-benzonitrile.

Workup

  1. stirringwas then stirred at room temperature for 20 mins
  2. customThe reaction mixture was quenched by addition of H2O
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-27fb7c4bdbfa4acda119d1dd682c4a8a
Source dataset
uspto-grants-2012_01
Patent number
US08088811B2

Reaction notes

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