3-Bromo-5-fluoro-2-methylaniline → N-(3-Bromo-5-fluoro-2-methyl-phenyl)-3-fluoro-terephthalamic acid methyl ester

HRID 589508Notes

Reaction equation

HRID 589508 reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([CH:6]=[C:7]([F:9])[CH:8]=1)[NH2:5].[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][C:17]([C:20](Cl)=[O:21])=[C:16]([F:23])[CH:15]=1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][C:17]([C:20]([NH:5][C:4]2[CH:6]=[C:7]([F:9])[CH:8]=[C:2]([Br:1])[C:3]=2[CH3:10])=[O:21])=[C:16]([F:23])[CH:15]=1

Participants

5

Reactant 2

HCID 27376413-Bromo-5-fluoro-2-methylanilineHCID 867310014-Chlorocarbonyl-3-fluoro-benzoic acid methyl ester

Product 1

HCID 71230752N-(3-Bromo-5-fluoro-2-methyl-phenyl)-3-fluoro-terephthalamic acid methyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

3-Bromo-5-fluoro-2-methylaniline (515 mg, 2.53 mmol) was dissolved in pyridine (20 ml). Then Intermediate 33 (547 mg, 2.53 mmol) and DMAP (3.09 mg, 0.025 mmol) were added and the resulting mixture was stirred at r.t. for 2 hrs. The solvents were removed in vacuo and the residue was taken up with EtOAc and H2O. The organic layer was washed with sat. NaHCO3 solution and brine, and then dried over Na2SO4. The solvents were removed in vacuo and the resulting residue was recrystallized with MeOH to afford Intermediate 34 as colorless solid.

Workup

  1. customThe solvents were removed in vacuo
  2. washThe organic layer was washed with sat. NaHCO3 solution and brine
  3. dry with materialdried over Na2SO4
  4. customThe solvents were removed in vacuo
  5. customthe resulting residue was recrystallized with MeOH

Sources & evidence

ORD record
ord-d92f6207ed644b728c3bb7cb677247ea
Source dataset
uspto-grants-2016_01
Patent number
US09233111B2

Reaction notes

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