Pyridine → Methyl 1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate

HRID 1662011Notes

Reaction equation

HRID 1662011 reaction equation
[O:1]=[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][NH:3]1.[F:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.N1C=CC=CC=1>C(Cl)Cl>[F:12][C:13]1[CH:18]=[CH:17][C:16]([N:3]2[CH:4]=[CH:5][CH:6]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[C:2]2=[O:1])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 2856454-Fluorophenylboronic acidHCID 579028Methyl 2-oxo-1,2-dihydropyridine-3-carboxylate

Product 1

HCID 21081723Methyl 1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of methyl 2-oxo-1,2-dihydropyridine-3-carboxylate (6.0 g, 39 mmol), 4-fluorophenylboronic acid (16.3 g, 116 mmol), cupric acetate (14 g, 78 mmol) and pyridine (12 g, 0.156 mol) in DCM (300 mL) is added 4 Å molecular sieves (5 g). The reaction mixture is stirred at RT overnight open to air. After the solids are filtered and washed with water, the filtrate is extracted with DCM (100 mL). The organic layer is dried over MgSO4 and concentrated. The residue is purified by silica gel column chromatography eluting with PE:DCM (2:1 to 0:1) to give the product (9.6 g, 100% yield). MS (m/z): 248.0 (M+H).

Workup

  1. additionis added 4 Å molecular sieves (5 g)
  2. filtrationAfter the solids are filtered
  3. washwashed with water
  4. extractionthe filtrate is extracted with DCM (100 mL)
  5. dry with materialThe organic layer is dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue is purified by silica gel column chromatography
  8. washeluting with PE

Sources & evidence

ORD record
ord-84a85a86a4884010920f8fa667b9e3e8
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

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