Pyridine → HCID 13105471, compound

HRID 1777516Notes

Reaction equation

HRID 1777516 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[F:13][C:14]([F:25])([F:24])[C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:13][C:14]([F:25])([F:24])[C:15]1[CH:20]=[C:19]([NH:1][C:2]2[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=2)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 11400Ethyl 3-aminobenzoateHCID 27343883-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 13105471HCID 13105471, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 3-aminobenzoate (0.300 g; 1.82 mmol), 3-(trifluoromethyl)phenylboronic acid (0.690 g; 3.63 mmol), copper acetate (0.660 g, 3.63 mmol) and pyridine (0.293 mL, 3.63 mmol) in dichloromethane (3 mL) was stirred at room temperature for 18 hours and filtered through celite and concentrated under reduced pressure. The residue was dissolved in water and extracted with ethyl acetate (2×200 mL). The organic layers were washed with brine, dried and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (eluent 5 to 40% ethyl acetate in heptane) to afford 0.334 g (60%) of ethyl 3-(3-(trifluoromethyl)phenylamino)benzoate.

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with ethyl acetate (2×200 mL)
  5. washThe organic layers were washed with brine
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by flash chromatography on silica gel (eluent 5 to 40% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-f8062f23279e44809607372c557ecc0d
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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