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

HRID 383372

반응식

HRID 383372 반응식
[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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매

반응 조건

온도
60 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-9dfeda01c4f647f5b767728a06bf0e0c
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367660B2

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