Diisopropylamine → HCID 136399883, compound

HRID 2388159Notes

Reaction equation

HRID 2388159 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:23])=[C:8]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[N:14][O:13][C:9]2=[C:10](Br)[N:11]=1)=[O:5])[CH3:2].[CH3:24][Si:25]([C:28]#[CH:29])([CH3:27])[CH3:26].C(NC(C)C)(C)C>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].[Cu]I.O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:23])=[C:8]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[N:14][O:13][C:9]2=[C:10]([C:29]#[C:28][Si:25]([CH3:27])([CH3:26])[CH3:24])[N:11]=1)=[O:5])[CH3:2]

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 66111TrimethylsilylacetyleneHCID 136399884HCID 136399884, compound

Product 1

HCID 136399883HCID 136399883, compoundYield 34.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-bromo-3-(4-chloro-phenyl)-4-hydroxy-isoxazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (150 mg, 0.38 mmol), tris(dibenzylideneacetone)dipalladium(0) (27 mg, 0.04 mmol), copper (I) iodide (14 mg, 0.08 mmol), trimethylsilylacetylene (107 μl, 0.76 mmol), diisopropylamine (321 μl, 2.27 mmol), and tetrahydrofuran (3.8 ml) was refluxed for eighteen hours before it was cooled to room temperature. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of hexanes and dichloromethane to give the title compound as a yellow solid (55 mg); MS (m/z): 415.34 (M+H+); 413.37 (M−H+).

Workup

  1. temperaturewas refluxed for eighteen hours before it
  2. customThe mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel with a gradient of hexanes and dichloromethane

Sources & evidence

ORD record
ord-68e0cea0b0894bc586e13e82d932d75e
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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