Sodium ethoxide → Ethyl 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

HRID 2364213Notes

Reaction equation

HRID 2364213 reaction equation
[CH2:1]([O:3][C:4](=[O:35])[CH2:5][C:6]([N:8]([C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)[C:9]1[C:10]([C:23]([O:25]CC)=O)=[N:11][CH:12]=[C:13]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:14]=1)=[O:7])[CH3:2].[O-]CC.[Na+]>C(O)C>[F:34][C:31]1[CH:32]=[CH:33][C:28]([N:8]2[C:9]3[C:10](=[N:11][CH:12]=[C:13]([CH2:15][C:16]4[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=4)[CH:14]=3)[C:23]([OH:25])=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:35])[C:6]2=[O:7])=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 69481480Ethyl 3-[(3-ethoxy-3-oxopropanoyl)(4-fluorophenyl)amino]-5-(4-fluorobenzyl)pyridine-2-carboxylate

Product 1

HCID 59799019Ethyl 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylateYield 85.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-[(3-ethoxy-3-oxopropanoyl)(4-fluorophenyl)amino]-5-(4-fluorobenzyl)pyridine-2-carboxylate (477 mg, 0.99 mmol) was dissolved in ethanol (50 mL) and sodium ethoxide (0.91 mL of a 2.4 M solution) was added. The solution was stirred until reaction was determined complete by LC-MS and the suspension was concentrated under reduced pressure. A small amount of water was added and the mixture was acidified with 1 N hydrochloric acid to a pH of 3 and the resulting white solid was collected by vacuum filtration to yield ethyl 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (368 mg, 85% yield). 1H NMR (methanol-d4/CDCl3) δ 8.19 (s, 1 H), 7.17-7.06 (m, 4 H), 6.94-6.83 (m, 4 H), 6.58 (s, 1 H), 4.26 (q, J=7.2 Hz, 2 H), 3.81 (s, 2 H), 1.27 (t, J=7.2 Hz, 3 H); MS m/z 459 (M+23).

Workup

  1. concentrationthe suspension was concentrated under reduced pressure
  2. additionA small amount of water was added
  3. filtrationthe resulting white solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-2bc18f2527ba4463a2dd9ae00317191d
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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