Pyridine → HCID 67974005, compound

HRID 1777528Notes

Reaction equation

HRID 1777528 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.N1C=CC=CC=1.[OH:17][C:18]1[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22]>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([O:17][C:18]2[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=2)[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:2]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 24522Ethyl 3-hydroxybenzoateHCID 27339503-Tolylboronic acid

Product 1

HCID 67974005HCID 67974005, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of m-tolylboronic acid (0.164 g; 1.20 mmol), copper acetate (0.219 g; 1.20 mmol), pyridine (0.097 mL; 1.20 mmol) and ethyl 3-hydroxybenzoate (0.100 g; 0.602 mmol) in dichloromethane (5 mL) was stirred at room temperature under nitrogen for 24 hours. The reaction mixture was filtered through celite, concentrated under reduced pressure and the residue purified by column chromatography on silica (eluent 2 to 20% ethyl acetate in heptane) to yield 0.084 g (54%) of the title compound which was used without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationconcentrated under reduced pressure
  3. customthe residue purified by column chromatography on silica (eluent 2 to 20% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-ba85df2673964a30a21e595edc418b9d
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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