Pyridine → HCID 12673494, compound

HRID 1592728Notes

Reaction equation

HRID 1592728 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[N:9]1[CH:14]=[CH:13][CH:12]=[C:11](B(O)O)[CH:10]=1.N1C=CC=CC=1.ClCCl>O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:11]1[CH:10]=[N:9][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 72442-BromophenolHCID 27343783-Pyridinylboronic acid

Product 1

HCID 12673494HCID 12673494, compoundYield 6%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 962WaterSolvent

Procedure

2-Bromophenol (355 mg, 2.05 mmol), 3-pyridyl-boronic acid (500 mg, 4.1 mmol), copper acetate (745 mg, 4.1 mmol) and pyridine (3.3 mL, 41 mmol) were added to dichloromethane (41 mL) and stirred for about 48 hours under air. The reaction was diluted with water (50 mL) and the layers separated. The organic layer was washed with 5N NaOH. The organic layer was concentrated, and chromatographed on silica gel (MeOH/dichloromethane) to yield 3-(2-bromo-phenoxy)-pyridine (30 mg, 6%) as a yellow oil. MS found 249.1 M+1. 3-(2-Bromo-phenoxy)-pyridine was coupled to piperazine using the Buchwald chemistry described in preparation 1A to afford the title compound. LRMS (ESI+): 256.1 (M+1)

Workup

  1. customthe layers separated
  2. washThe organic layer was washed with 5N NaOH
  3. concentrationThe organic layer was concentrated
  4. customchromatographed on silica gel (MeOH/dichloromethane)

Sources & evidence

ORD record
ord-15780cdd69714f9aa79fd742f6eee012
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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