Triethylamine → HCID 69217716, compound

HRID 1394641Notes

Reaction equation

HRID 1394641 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])/[CH:2]=[CH:3]/[CH3:4].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C.Br[C:38]1[CH:39]=[CH:40][C:41]2[O:45][N:44]=[C:43]([C:46]3[CH:51]=[C:50]([CH:52]([CH3:54])[CH3:53])[CH:49]=[C:48]([CH:55]([CH3:57])[CH3:56])[C:47]=3[O:58][CH2:59][CH3:60])[C:42]=2[CH:61]=1>CN(C=O)C.[Cl-].[Na+].O.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]>[CH3:7][O:6][C:1](=[O:5])[CH:2]=[C:3]([C:38]1[CH:39]=[CH:40][C:41]2[O:45][N:44]=[C:43]([C:46]3[CH:51]=[C:50]([CH:52]([CH3:53])[CH3:54])[CH:49]=[C:48]([CH:55]([CH3:56])[CH3:57])[C:47]=3[O:58][CH2:59][CH3:60])[C:42]=2[CH:61]=1)[CH3:4]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 638132Methyl CrotonateHCID 17952726HCID 17952726, compound

Product 1

HCID 69217716HCID 69217716, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
120 °C

Procedure

Methyl crotonate (0.087 ml, 0.82 mmol), tris(dibenzylideneacetone)-dipalladium(0) (6.8 mg, 0.007 mmol), tri-o-tolylphosphine (91 mg, 0.30 mmol), and triethyl amine (0.208 ml, 1.5 mmol) was added to a solution of 5-bromo-3-(2-ethoxy-3,5-diisopropyl-phenyl)-benzo[d]isoxazole (300 mg, 0.75 mmol) in DMF (5 ml). The reaction mixture was then heated to 120° C. under an atmosphere of nitrogen. After 12 h, the reaction was cooled and poured into brine, then extracted with ethyl acetate (2×10 mL). The organic layer was dried over MgSO4 and evaporated to a residue. The residue was purified by silica gel chromatography (5% ethyl acetate in hexanes) to give 3-[3-(2-ethoxy-3,5-diisopropyl-phenyl)-benzo[d]isoxazol-5-yl]-but-2-enoic acid methyl ester as a clear oil (99.6 mg, 32%).

Workup

  1. temperaturethe reaction was cooled
  2. extractionextracted with ethyl acetate (2×10 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated to a residue
  5. customThe residue was purified by silica gel chromatography (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-b1c24f8338f04e4394fed72332a72fa2
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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