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

HRID 2375752ノート

反応式

HRID 2375752 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bb58a19b295b46fab7c49a680e528f57
出典データセット
uspto-grants-2008_12
特許番号
US07465809B2

反応ノート

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