Dimethylformamide → HCID 21942546, compound

HRID 1096941Notes

Reaction equation

HRID 1096941 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:11]=[C:12](OS(C(F)(F)F)(=O)=O)[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])[CH3:2].[CH3:22][N:23](C=O)C>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:22]([C:12]1[CH:11]=[C:6]([CH:5]=[C:4]([O:3][CH2:1][CH3:2])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])#[N:23]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 57930910HCID 57930910, compound

Product 1

HCID 21942546HCID 21942546, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 3-ethoxy-5-trifluoromethanesulfonyloxybenzoate (308 mg, 0.94 mmol), zinc cyanide (165 mg, 1.41 mmol), tetrakis(triphenylphosphine)palladium(0) (54 mg, 0.05 mmol) and DMF (2.0 mL) was stirred in a nitrogen atmosphere at 80° C. for 12 hours. After left cooled, the reaction mixture was diluted with ethyl acetate (30 mL), washed with aqueous 14% ammonia and aqueous saturated sodium chloride solution, dried with sodium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography to obtain the title compound as a colorless solid.

Workup

  1. waitAfter left
  2. temperaturecooled
  3. washwashed with aqueous 14% ammonia and aqueous saturated sodium chloride solution
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-72a347b9fa904d5dad72e8110d081e2b
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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