Dimethylformamide → HCID 90413214, compound

HRID 1522023Notes

Reaction equation

HRID 1522023 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[N:9]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:10]=[C:11](I)[C:3]=12.[CH3:21][N:22](C)C=O>O.[C-]#N.[Zn+2].[C-]#N.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].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]>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[N:9]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:10]=[C:11]([C:21]#[N:22])[C:3]=12

Participants

7

Reactant 2

HCID 6228DimethylformamideHCID 90413560HCID 90413560, compound

Product 1

HCID 90413214HCID 90413214, compound

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of Example 263B (2.5 g, 5.86 mmol), zinc cyanide (0.8 g, 7.0 mmol), 1,1′-bis(diphenylphosphino)ferrocene (0.4 g, 0.7 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.27 g, 0.3 mmol) in N,N-dimethylformamide (50 mL) and water (0.5 mL) was flushed with nitrogen and heated at 80° C. overnight. The reaction was quenched with brine and extracted with ethyl acetate (twice). The organic phase was concentrated and purified by flash chromatography (silica gel, 30% ethyl acetate in hexane) to afford the title compound. MS (ESI+) m/z 326 (M+H)+.

Workup

  1. customThe reaction was quenched with brine
  2. extractionextracted with ethyl acetate (twice)
  3. concentrationThe organic phase was concentrated
  4. custompurified by flash chromatography (silica gel, 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-e192d597ab524014b93a37a2d13ebe09
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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