Pyridine → methyl 4-(3-Fluorophenylamino)benzoate

HRID 1777576Notes

Reaction equation

HRID 1777576 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[F:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:12][C:13]1[CH:18]=[C:17]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=2)[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 12082Methyl 4-aminobenzoateHCID 27339863-Fluorophenylboronic acid

Product 1

HCID 67974249methyl 4-(3-Fluorophenylamino)benzoate

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 4-aminobenzoate (0.500 g; 3.31 mmol), 3-fluorobenzeneboronic acid (0.925 g; 6.62 mmol), copper acetate (1.20 g; 6.62 mmol) and pyridine (0.535 mL; 6.62 mmol) in dichloromethane (15 mL) was stirred at room temperature overnight. The reaction mixture was filtered and concentrated under reduced pressure.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-643dd0b905d74948944b674714561828
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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