HCID 57586440, compound → HCID 57905901, compound

HRID 1670155Notes

Reaction equation

HRID 1670155 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[C:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]#[CH:25])=[CH:17][CH:16]=[CH:15][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])([OH:3])=[O:2].[Br:26][C:27]1[CH:28]=[C:29]([CH:35]=[C:36](I)[CH:37]=1)[C:30]([N:32]([CH3:34])[CH3:33])=[O:31]>C1COCC1.C(O)(C(F)(F)F)=O.[Cu]I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:26][C:27]1[CH:37]=[C:36]([C:25]#[C:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][C:18]2[C:6]([CH2:5][CH2:4][C:1]([OH:3])=[O:2])=[C:7]([CH:15]=[CH:16][CH:17]=2)[O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH:35]=[C:29]([C:30](=[O:31])[N:32]([CH3:33])[CH3:34])[CH:28]=1

Participants

7

Reactant 2

HCID 57586440HCID 57586440, compoundHCID 57905910HCID 57905910, compound

Product 1

HCID 57905901HCID 57905901, compoundYield 65.8%

Reagents, catalysts & solvents 4

HCID 6422Trifluoroacetic acidCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-[2-(2-carboxy-ethyl)-3-hept-6-ynyl-phenoxy]-butyric acid (900 mg, 2.6 mmol), 3-bromo-5-iodo-N,N-dimethyl-benzamide (1.0 g, 2.8 mmol), CuI (20 mg, 0.11 mmol) in THF (10 mL) and TEA (10 mL) was added bis(triphenylphosphine) palladium(II) dichloride (75 mg, 0.11 mmol). The reaction mixture was heated at 70° C. for 5 h. Then the reaction mixture was cooled to room temperature, a few drops of TFA were added and the resulting mixture was concentrated under reduced pressure. The crude material was purified by column chromatography (Isco™ 120 g) using ethyl acetate as eluting solvent to give the title compound (980 mg, 65%) as an oil.

Workup

  1. temperatureThen the reaction mixture was cooled to room temperature
  2. concentrationthe resulting mixture was concentrated under reduced pressure
  3. customThe crude material was purified by column chromatography (Isco™ 120 g)
  4. washas eluting solvent

Sources & evidence

ORD record
ord-30cf87baf9d8496dbb73cc0e1cea1226
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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