Pyridine → Methyl 6-Oxo-1-phenyl-1,6-dihydropyridine-3-carboxylate

HRID 870802Notes

Reaction equation

HRID 870802 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](=[O:11])[NH:7][CH:6]=1)=[O:4].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CC=CC=1>ClCCl.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](=[O:11])[N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 1049PyridineHCID 66827Phenylboronic AcidHCID 416343Methyl 6-oxo-1,6-dihydropyridine-3-carboxylate

Product 1

HCID 11989075Methyl 6-Oxo-1-phenyl-1,6-dihydropyridine-3-carboxylateYield 56%

Reagents, catalysts & solvents 2

HCID 165397Cupric acetate monohydrateCatalystHCID 6344DichloromethaneSolvent

Procedure

Methyl-6-oxo-1,6-dihydropyridine-3-carboxylate (6.0 g, 39.22 mmol), phenylboronic acid (5.74 g, 47.06 mmol), copper(II) acetate monohydrate (11.76 g, 58.82 mmol), pyridine (6.32 mL, 78.43 mmol) and molecular sieves (4 Å, 6.0 g) in dichloromethane (100 mL) was stirred at ambient temperature for 12 hours and filtered. Standard extractive work up provided a crude residue which was purified by silica gel column chromatography (100-200 mesh) (1-2% methanol in chloroform) to give the title compound as a brown solid (5.0 g, 56%). m.p. 100-105° C.; 1H NMR (400 MHz, CDCl3) δ 3.86 (s, 3H), 6.63 (d, J=9.5 Hz, 1H), 7.36-7.55 (m, 5H), 7.91 (dd, J=2.5, 9.9 Hz, 1H), 8.23 (d, J=2.5 Hz, 1H); IR (KBr) ν 3058, 2924, 2854, 1721, 1675, 1540, 1446, 1313, 1271, 1103 cm−1; MS 230 (M+1).

Workup

  1. filtrationfiltered
  2. customStandard extractive work up provided a crude residue which
  3. customwas purified by silica gel column chromatography (100-200 mesh) (1-2% methanol in chloroform)

Sources & evidence

ORD record
ord-e6aa1c34fc614d28ace763b07c2b902a
Source dataset
uspto-grants-2015_03
Patent number
US08969575B2

Reaction notes

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