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

HRID 471942Notes

Reaction equation

[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

Participants

Conditions

Temperature: 60 °C

Procedure

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]+.

Workup

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

Sources & evidence

ORD record: ord-4ec0e294b75f4e0995e6bffbc3855044
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633189B2

Reaction notes

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