Oxazole → HCID 68816107, compound

HRID 732492

Reaction equation

HRID 732492 reaction equation
C([Li])CCC.[O:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[CH3:11][O:12][C:13](=[O:28])[C:14]1[CH:26]=[C:25](I)[CH:24]=[C:16]([C:17]([N:19]([CH3:23])[CH2:20][CH2:21][CH3:22])=[O:18])[CH:15]=1>C1COCC1.C(OCC)C.[Cl-].[Zn+2].[Cl-].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:11][O:12][C:13](=[O:28])[C:14]1[CH:26]=[C:25]([C:7]2[O:6][CH:10]=[CH:9][N:8]=2)[CH:24]=[C:16]([C:17]([N:19]([CH3:23])[CH2:20][CH2:21][CH3:22])=[O:18])[CH:15]=1

Participants

8

Reactant 3

HCID 9255OxazoleHCID 21086185Methyl 3-iodo-5-{[methyl(propyl)amino]carbonyl}benzoateHCID 178418339Butyllithium

Product 1

HCID 68816107HCID 68816107, compoundYield 82%

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Add n-butyllithium (1.6 M in hexanes, 1.25 mL, 2.01 mmol) dropwise to a solution of oxazole (126 mg, 1.83 mmol) in THF (12.6 mL) at −78° C. Stir for 30 min at −78° C. and add a solution of zinc chloride (747 mg, 5.49 mmol) in diethyl ether (5.5 mL) and stir at 0° C. for 1 h. Add a solution of 5-iodo-N-methyl-N-propyl-isophthalamic acid methyl ester (330 mg, 0.91 mmol) in THF (5.1 mL) followed by tetrakis(triphenylphosphine)palladium (0) (105 mg, 0.091 mmol) and heat to reflux for 30 min. Add ethyl acetate (40 mL), wash with water (2×20 mL), dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 50:50 ethyl acetate:hexane) to give the title compound (225 mg, 82%).

Workup

  1. stirringstir at 0° C. for 1 h
  2. temperatureheat
  3. temperatureto reflux for 30 min
  4. washAdd ethyl acetate (40 mL), wash with water (2×20 mL)
  5. dry with materialdry (magnesium sulfate)
  6. concentrationconcentrate
  7. custompurify
  8. wash(silica gel chromatography, eluting with 50:50 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-212d4cacf3a84ebda025b0d1763030c4
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Linked notes

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