Diethyl Ether → (2-Diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(2,4-dichlorophenyl)oxindole

HRID 1369107Notes

Reaction equation

HRID 1369107 reaction equation
[CH2:1]([N:3]([CH2:22][CH3:23])[CH2:4][CH2:5][N:6]1[C:16]2[C:11](=[C:12]([C:18]([F:21])([F:20])[F:19])[CH:13]=[C:14]([I:17])[CH:15]=2)[C:9](=[O:10])[C:7]1=[O:8])[CH3:2].C(OCC)C.[Cl:29][C:30]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:31]=1[Mg]I>C1(C)C=CC=CC=1>[CH2:22]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[C:16]2[C:11](=[C:12]([C:18]([F:20])([F:21])[F:19])[CH:13]=[C:14]([I:17])[CH:15]=2)[C:9]([OH:10])([C:33]2[CH:32]=[CH:31][C:30]([Cl:29])=[CH:35][C:34]=2[Cl:36])[C:7]1=[O:8])[CH3:23]

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 110265521-(2-Diethylaminoethyl)-4-trifluoromethyl-6-iodoisatinHCID 178478195HCID 178478195, compound

Product 1

HCID 18518587(2-Diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(2,4-dichlorophenyl)oxindoleYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-(2-diethylaminoethyl)-4-trifluoromethyl-6-iodoisatin (150 mg, 0.341 mmol) in a mixed solvent of diethyl ether (2 mL) and toluene (1 mL) was added dropwise a freshly prepared 0.794 N 2,4-dichlorophenyl magnesium iodide in ether (0.45 mL, 0.387 mmol) at room temperature. The mixture was stirred for 1 h at the same temperature and the reaction was quenched with aqueous NaHCO3. The mixture was extracted with ethyl acetate and the extracts were dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography with 80:1 to 50:1 chloroform/methanol to give the title compound (111 mg, 55%).

Workup

  1. customthe reaction was quenched with aqueous NaHCO3
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe extracts were dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography with 80:1 to 50:1 chloroform/methanol

Sources & evidence

ORD record
ord-b3b0c918f81844a7bc053ce6ba85c300
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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