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Cesium carbonate → Ethyl 5-ethyl-2-(4-nitrophenyl)-1,3-oxazole-4-carboxylate

HRID 43583
Notes
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Reaction equation

HRID 43583 reaction equation
[CH2:1]([C:3]1[O:7][CH:6]=[N:5][C:4]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:2].I[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCOCC1>[CH2:1]([C:3]1[O:7][C:6]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[N:5][C:4]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 124951-Iodo-4-nitrobenzeneHCID 80271Tri-o-tolylphosphineHCID 122141024-Oxazolecarboxylic acid, 5-ethyl-, ethyl ester

Product 1

HCID 68406117Ethyl 5-ethyl-2-(4-nitrophenyl)-1,3-oxazole-4-carboxylateYield 37.2%

Reagents, catalysts & solvents 3

HCID 167845
palladium(II) acetate
Catalyst
HCID 962WaterSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Dioxane (30 mL) was added to ethyl 5-ethyl-1,3-oxazole-4-carboxylate (described in Armarego, Wilfred L. F.; Taguchi, Hiroyasu; Cotton, Richard G. H.; Battiston, Sandra; Leong, Lillian; Eur. J. Med. Chem. Chim. Ther.; 22; 1987; 283-292, 1.69 g, 10 mmol), 1-iodo-4-nitrobenzene (2.74 g, 11 mmol), palladium acetate (179.6 mg, 0.8 mmol), tris(2-methylphenyl)phosphine (0.49 g, 1.6 mmol) and cesium carbonate (3.25 g, 10 mmol), and the mixture was stirred at 100° C. for 13 hours. Water was added, followed by extraction with ethyl acetate and washing with brine. This was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=5/1, 3/1, 2/1) to obtain 1.08 g of the title compound as a colorless solid (37%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washwashing with brine
  3. dry with materialThis was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=5/1, 3/1, 2/1)

Sources & evidence

ORD record
ord-90ceebe8cc994cf6baf0a2a04633192b
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08536197B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes