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

HRID 643683Notes

Reaction equation

HRID 643683 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-e0b64062958648258361e84a30844659
Source dataset
uspto-grants-2010_04
Patent number
US07700622B2

Reaction notes

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