Triethylamine → 4-Ethoxycarbonyl-5-methyl-3-(2-iodo-6-fluoro-phenyl)isoxazole

HRID 434054Notes

Reaction equation

HRID 434054 reaction equation
[I:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:3]=1[C:4](=[N:6][OH:7])Cl.[CH2:13]([O:15][C:16](=[O:20])[C:17]#[C:18][CH3:19])[CH3:14].CCN(CC)CC>CCOCC>[CH2:13]([O:15][C:16]([C:17]1[C:4]([C:3]2[C:8]([F:12])=[CH:9][CH:10]=[CH:11][C:2]=2[I:1])=[N:6][O:7][C:18]=1[CH3:19])=[O:20])[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78043Ethyl 2-butynoateHCID 591193512-Iodo-6-fluorobenzoyl chloride oxime

Product 1

HCID 227138064-Ethoxycarbonyl-5-methyl-3-(2-iodo-6-fluoro-phenyl)isoxazoleYield 82%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a solution of 2-iodo-6-fluorobenzoyl chloride oxime (26.6 mmol) and ethyl-2-butynoate (3.72 ml, 31.92 ml, 1.2 eq.) in Et2O (106 ml) under N2, stirring at 0-5° C. added dropwise a solution of Et3N (4.81 ml, 34.6 mmol, 1.3 eq) in Et2O (13 ml) over 1 h. The reaction was allowed to warm to room temperature and stirred overnight. Et2O was added and then washed with H2O, brine, dried (MgSO4), filtered, and concentrated. The crude residue was chromatographed on silica gel using ethyl acetate in hexanes (1-20%) to give the title compound (8.21 g, 82%).

Workup

  1. washwashed with H2O, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-0d84eef45a6b40cb9a73fbe4f691b8b0
Source dataset
uspto-grants-2003_12
Patent number
US06670373B1

Reaction notes

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