Water → diethyl ((E)-2-{3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)(methyl)amino]-1-phenyl-1H-pyrazol-4-yl}ethenyl)phosphonate

HRID 2222016

Reaction equation

HRID 2222016 reaction equation
[CH2:1]([P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])P(=O)(OCC)OCC.[H-].[Na+].[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25]1[O:26][C:27]([CH3:56])=[C:28]([CH2:30][O:31][C:32]2[CH:53]=[CH:52][C:35]([CH2:36][N:37]([CH3:51])[C:38]3[C:42]([CH:43]=O)=[CH:41][N:40]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[N:39]=3)=[CH:34][C:33]=2[O:54][CH3:55])[N:29]=1.O>CN(C)C=O>[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25]1[O:26][C:27]([CH3:56])=[C:28]([CH2:30][O:31][C:32]2[CH:53]=[CH:52][C:35]([CH2:36][N:37]([CH3:51])[C:38]3[C:42](/[CH:43]=[CH:1]/[P:10](=[O:17])([O:11][CH2:12][CH3:13])[O:14][CH2:15][CH3:16])=[CH:41][N:40]([C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)[N:39]=3)=[CH:34][C:33]=2[O:54][CH3:55])[N:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 15455Tetraethyl methylenediphosphonateHCID 24758Sodium hydrideHCID 866059253-([4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl](methyl)amino)-1-phenyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 86605926diethyl ((E)-2-{3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)(methyl)amino]-1-phenyl-1H-pyrazol-4-yl}ethenyl)phosphonateYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tetraethyl methylenediphosphonate (63 mg) in N,N-dimethylformamide (3 mL) was added sodium hydride (60% in oil, 8.8 mg) at room temperature, and the mixture was stirred for 30 min. To the reaction mixture was added 3-([4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl](methyl)amino)-1-phenyl-1H-pyrazole-4-carbaldehyde (100 mg) and the mixture was further stirred at room temperature for 2 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to flash silica gel column chromatography and eluted with ethyl acetate-hexane (1:1 to 4:1, v/v) to give diethyl ((E)-2-{3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)(methyl)amino]-1-phenyl-1H-pyrazol-4-yl}ethenyl)phosphonate as a colorless oil (84.9 mg, yield 67%).

Workup

  1. stirringthe mixture was further stirred at room temperature for 2 hrs
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. washeluted with ethyl acetate-hexane (1:1 to 4:1

Sources & evidence

ORD record
ord-bc0ea54d27584d1198cabb98de70f736
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Linked notes

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