Water → 3-(4-fluoro-2-nitrophenyl)-N,N-dimethylprop-2-yn-1-amine

HRID 383372

反応式

HRID 383372 の反応式
[CH3:1][N:2]([CH3:6])[CH2:3][C:4]#[CH:5].BrC1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10]C=1[N+]([O-])=O.C([N:20]([CH2:23][CH3:24])CC)C.CN(C=[O:29])C.[OH2:30]>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.[Cu]I>[F:14][C:12]1[CH:11]=[CH:10][C:24]([C:5]#[C:4][CH2:3][N:2]([CH3:6])[CH3:1])=[C:23]([N+:20]([O-:29])=[O:30])[CH:13]=1

参加物

8

反応物 5

HCID 962WaterHCID 6228DimethylformamideHCID 8471TriethylamineHCID 81643N,N-DimethylpropargylamineHCID 27569932-Bromo-4-fluoro-1-nitrobenzene

生成物 1

HCID 675372373-(4-fluoro-2-nitrophenyl)-N,N-dimethylprop-2-yn-1-amine収率 68%

試薬・触媒・溶媒 2

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

反応条件

温度
60 °C

実験手順

To a flask charged with N,N-dimethylprop-2-yn-1-amine (737 mg, 945 μL, 8.86 mmol), 2-bromo-4-fluoro-1-nitrobenzene (1300 mg, 5.91 mmol), PdCl2(PPh3)2 (415 mg, 0.59 mmol), CuI (169 mg, 0.89 mmol) were added triethylamine (2.47 mL, 17.73 mmol) and DMF (10 mL) under N2 atmosphere. The reaction mixture was heated at 60° C. for 5 h, then poured into water (300 mL) and extracted with ethyl acetate (3×40 mL). The organic fractions were combined, dried over MgSO4, filtered, and concentrated in vacuo. Purification by silica gel chromatography (50-100% ethyl acetate/hexanes) yielded 3-(4-fluoro-2-nitrophenyl)-N,N-dimethylprop-2-yn-1-amine (895 mg, 68% yield). LC/MS m/z 223.0 [M+H]+.

後処理

  1. extractionextracted with ethyl acetate (3×40 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel chromatography (50-100% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-9dfeda01c4f647f5b767728a06bf0e0c
出典データセット
uspto-grants-2013_02
特許番号
US08367660B2

関連ノート

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