Triethylamine → 4-Bromo-2-{[(4-methoxyphenyl)methyl]amino}benzonitrile

HRID 2354611Notes

Reaction equation

HRID 2354611 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4]C(F)=[C:6]([CH:9]=1)C#N.[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1.C([N:23]([CH2:26][CH3:27])CC)C>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:27]([C:26]#[N:23])=[C:6]([NH:18][CH2:17][C:16]2[CH:19]=[CH:20][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 754524-MethoxybenzylamineHCID 27249005-Bromo-2-fluorobenzonitrile

Product 1

HCID 592630054-Bromo-2-{[(4-methoxyphenyl)methyl]amino}benzonitrileYield 81%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 5-bromo-2-fluorobenzonitrile (3 g), 4-methoxybenzylamine (2.2 g), and triethyl amine (3 ml) in DMSO (5 ml) was heated at 120° C. for 5 h. The solution was partitioned between water and ethyl acetate. The combined organic extract was washed with brine, dried over Na2SO4 and concentrated. The residue was chromatographed to give the desired product (2.6 g, 81%) HPLC (6 minute gradient) tR=4.33 min; MS m/z 315.09, 317.08 (M+H]+

Workup

  1. customThe solution was partitioned between water and ethyl acetate
  2. extractionThe combined organic extract
  3. washwas washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was chromatographed

Sources & evidence

ORD record
ord-493a92c0c6d148db9c336d99b57d361a
Source dataset
uspto-grants-2010_07
Patent number
US07754726B2

Reaction notes

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