Diisopropylethylamine → Methyl 3-[(5-bromo-2-fluoro-benzoyl)amino]-2,4-dimethyl-benzoate

HRID 239928Notes

Reaction equation

HRID 239928 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[NH2:12][C:13]1[C:14]([CH3:24])=[C:15]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:16]([O:18][CH3:19])=[O:17].C(N(CC)C(C)C)(C)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([NH:12][C:13]1[C:14]([CH3:24])=[C:15]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:16]([O:18][CH3:19])=[O:17])=[O:9]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 27363155-Bromo-2-fluorobenzoic acidHCID 66871802Methyl 3-amino-2,4-dimethylbenzoate

Product 1

HCID 86707315Methyl 3-[(5-bromo-2-fluoro-benzoyl)amino]-2,4-dimethyl-benzoateYield 51.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-2-fluoro-benzoic acid (500 mg, 2.28 mmol) in CH2Cl2 (15 mL) at 0° C. are added methyl 3-amino-2,4-dimethylbenzoate (409 mg, 2.28 mmol, see preparation 10) and N,N-diisopropylethylamine (737.6 mg, 5.71 mmol). After stirring the reaction mixture for 10 minutes, 1-propanephosphonic acid cyclic anhydride (50% solution in ethyl acetate, 1.74 g, 2.74 mmol) is added via syringe and stirred at 50° C. After 16 hours, the solvent is removed under reduced pressure and the residue is triturated with MeOH to give the title compound as a white solid (450 mg, 51.8%). Mass spectrum (m/z): 380.2 (M+1).

Workup

  1. stirringstirred at 50° C
  2. waitAfter 16 hours
  3. customthe solvent is removed under reduced pressure
  4. customthe residue is triturated with MeOH

Sources & evidence

ORD record
ord-2005289480dc4e7e994c4b220b12c802
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

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