Pyridine → HCID 22319011, compound

HRID 415916Notes

Reaction equation

HRID 415916 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:5](=[O:8])[NH:6][CH:7]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:5](=[O:8])[N:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 66827Phenylboronic AcidHCID 2763337Methyl 5-bromo-2-hydroxynicotinate

Product 1

HCID 22319011HCID 22319011, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A round bottom flask was charged with methyl 5-bromo-2-oxo-1,2-dihydropyridine-3-carboxylate (0.500 g, 2.2 mmol), phenylboronic acid (0.66 g, 5.4 mmol), and copper(II) acetate (0.78 g, 4.3 mmol). Dichloromethane (25 mL) was added, followed by 4 A molecular sieves (500 mg, activated) and pyridine (0.70 mL, 8.6 mmol). The reaction mixture was stirred overnight at room temperature in the presence of air. The reaction mixture was diluted with dichloromethane and filtered through a small pad of Celite, washing well with dichloromethane. The filtrate was concentrated under vacuum. The remaining residue was purified by silica gel chromatography (1% methanol/dichloromethane) to give methyl 5-bromo-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxylate as a yellow foam/oil (0.655 g, 1.9 mmol, 89% yield). MS (ESI pos. ion) m/z: 309 (MH+). Calc'd exact mass for C13H10BrNO3: 308.

Workup

  1. filtrationfiltered through a small pad of Celite
  2. washwashing well with dichloromethane
  3. concentrationThe filtrate was concentrated under vacuum
  4. customThe remaining residue was purified by silica gel chromatography (1% methanol/dichloromethane)

Sources & evidence

ORD record
ord-7a976d183c4e4574af7b1e77fa02812c
Source dataset
uspto-grants-2012_01
Patent number
US08088794B2

Reaction notes

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