Triethylamine → Methyl 5-bromo-2-(2-(3-(trifluoromethyl)phenyl)acetamido)benzoate

HRID 1478478Notes

Reaction equation

HRID 1478478 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH2:9][C:10](Cl)=[O:11])[CH:6]=[CH:7][CH:8]=1.[NH2:15][C:16]1[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19].C(N(CC)CC)C>C(Cl)Cl>[Br:26][C:23]1[CH:24]=[CH:25][C:16]([NH:15][C:10](=[O:11])[CH2:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:14])([F:13])[F:1])[CH:4]=2)=[C:17]([CH:22]=1)[C:18]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 736224Methyl 2-amino-5-bromobenzoateHCID 127516363-(Trifluoromethyl)phenylacetyl chloride

Product 1

HCID 118005521Methyl 5-bromo-2-(2-(3-(trifluoromethyl)phenyl)acetamido)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3-(trifluoromethyl)phenyl)acetyl chloride (23.4 mmol assuming quantitative yield in previous step, Intermediate 5: step a) in DCM (50 mL) in an ice bath was added methyl 2-amino-5-bromobenzoate (4.90 g, 21.3 mmol) followed by triethylamine (6.51 mL, 46.8 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was washed with saturated aqueous NH4Cl then water. The organic phase was dried (Na2SO4), filtered, and concentrated and the residue was purified by flash column chromatography (50-70% DCM-heptanes). Some of the title compound was obtained in pure form from the column, along with mixed fractions containing the title compound and the starting aniline. The mixed fractions were left to stand in DCM:heptanes (1:1) overnight, forming crystalline needles of the title compound, which were collected by vacuum filtration and combined with clean fractions from the column.

Workup

  1. washThe reaction mixture was washed with saturated aqueous NH4Cl
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified by flash column chromatography (50-70% DCM-heptanes)

Sources & evidence

ORD record
ord-a8ff32122d1549f693ce2a6bbabc72f0
Source dataset
uspto-grants-2016_08
Patent number
US09403816B2

Reaction notes

Loading…