Dimethylacetamide → HCID 136399882, compound

HRID 2388157Notes

Reaction equation

HRID 2388157 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:22])=[C:8]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:14][O:13][C:9]2=[C:10](Br)[N:11]=1)=[O:5])[CH3:2].C[C:24]([N:26](C)C)=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].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[C-]#N.[Zn+2].[C-]#N.[Zn]>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:22])=[C:8]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:14][O:13][C:9]2=[C:10]([C:24]#[N:26])[N:11]=1)=[O:5])[CH3:2]

Participants

7

Reactant 2

HCID 31374DimethylacetamideHCID 136399879HCID 136399879, compound

Product 1

HCID 136399882HCID 136399882, compound

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
120 °C

Procedure

A mixture of 7-bromo-4-hydroxy-3-phenyl-isoxazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (57.3 mg, 0.16 mmol), tris(dibenzylideneacetone)dipalladium(0) (29 mg, 0.03 mmol), 1,1′-bis(diphenylphosphino)ferrocene (35 mg, 0.06 mmol), zinc cyanide (10 mg, 0.09 mmol), zinc (1 mg, 0.02 mmol), and dimethylacetamide (0.32 ml) was stirred at 120° C. for two hours before it was cooled to room temperature, quenched with water, and filtered. The filtrate 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 ethyl acetate and dichloromethane to give the title compound as a brown solid (19 mg); MS (m/z): 310.31 (M+H+); 308.31 (M−H+).

Workup

  1. temperaturewas cooled to room temperature
  2. customquenched with water
  3. filtrationfiltered
  4. customThe filtrate was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane

Sources & evidence

ORD record
ord-644a6e77798e45c7898e1a1115e040cd
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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