Water → HCID 67982928, compound

HRID 2176423Notes

Reaction equation

HRID 2176423 reaction equation
Br[C:2]1[CH:10]=[C:9]([Cl:11])[C:5]([N:6]([CH3:8])[CH3:7])=[C:4]([Cl:12])[CH:3]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C[Si]([CH2:59][C:60]#[N:61])(C)C.O>CN(C=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].[F-].[Zn+2].[F-].C(OCC)(=O)C>[Cl:12][C:4]1[CH:3]=[C:2]([CH2:59][C:60]#[N:61])[CH:10]=[C:9]([Cl:11])[C:5]=1[N:6]([CH3:8])[CH3:7]

Participants

9

Reactant 4

HCID 962WaterHCID 87557(Trimethylsilyl)acetonitrileHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 16091233HCID 16091233, compound

Product 1

HCID 67982928HCID 67982928, compound

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 10129912Zinc(II) fluorideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

In a glass tube with screw-on lid, 2 g (7.43 mmol) of 4-bromo-2,6-dichloro-N,N-dimethylaniline (known from European Journal of Organic Chemistry (2006), (19), 4398-4404) are initially charged with 86 mg (0.14 mmol) of xantphos and 136 mg (0.14 mmol) of tris(dibenzylideneacetone)-dipalladium in 10 ml of DMF. 1.01 g (8.92 mmol) of trimethylsilylacetonitrile and 0.46 g (4.46 mmol) of zinc fluoride are then added, and in the closed vessel the reaction is heated at 90° C. for 16 hours. The reaction mixture is cooled, water and ethyl acetate are added and the mixture is filtered through silica gel.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationthe mixture is filtered through silica gel

Sources & evidence

ORD record
ord-8e80297d774e41188f84b2de32e9765c
Source dataset
uspto-grants-2015_06
Patent number
US09066945B2

Reaction notes

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