Dimethylformamide → HCID 86692164, compound

HRID 2201757Notes

Reaction equation

HRID 2201757 reaction equation
[CH3:1][N:2](C=O)C.FC(F)(S(O[C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[C:27](=[O:31])[NH:26][CH:25]2[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=O)=O)C(F)(F)C(F)(F)C(F)(F)F>C(OCC)(=O)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].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].[Zn].[C-]#N.[Zn+2].[C-]#N>[CH2:32]([CH:25]1[C:24]2[C:28](=[CH:29][CH:30]=[C:22]([C:1]#[N:2])[CH:23]=2)[C:27](=[O:31])[NH:26]1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

8

Reactant 2

HCID 6228DimethylformamideHCID 86692163HCID 86692163, compound

Product 1

HCID 86692164HCID 86692164, compoundYield 43%

Reagents, catalysts & solvents 5

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a round bottom flask was added 12 mL of DMF. This was degassed with N2 for 10 min and then added 3-benzyl-1-oxoisoindolin-5-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate (609 mg, 1.17 mmol), tris(dibenzylideneacetone)dipalladium(0) (214 mg, 0.23 mmol), 1,1′-bis(diphenylphosphino)ferrocene (142 mg, 0.26 mmol) and zinc (30.6 mg, 0.47 mmol) respectively. This was heated up to 100° C. for 15 min under N2, then added Zinc cyanide (82 mg, 0.70 mmol). This was heated at 100° C. for 2.5 hours, LC/MS showed complete conversion. The reaction mixture was cooled down to room temperature, diluted with ethyl acetate, then filtered through a pad of celite, the filtrate was concentrated down and the residue was purified by flash-chromatography on silica gel with 30-90% ethyl acetate in hexane, 125 mg (43%) of the product was obtained.

Workup

  1. customThis was degassed with N2 for 10 min
  2. temperatureThis was heated at 100° C. for 2.5 hours
  3. temperatureThe reaction mixture was cooled down to room temperature
  4. filtrationfiltered through a pad of celite
  5. concentrationthe filtrate was concentrated down
  6. customthe residue was purified by flash-chromatography on silica gel with 30-90% ethyl acetate in hexane

Sources & evidence

ORD record
ord-b6c783c67921411f8ad2c734daf29d51
Source dataset
uspto-grants-2016_06
Patent number
US09365512B2

Reaction notes

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