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

HRID 505597노트

반응식

HRID 505597 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-30a803721c5440cb9a20ec2fc49dae14
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781473B2

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