Water → HCID 59212606, compound

HRID 2243881Notes

Reaction equation

HRID 2243881 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13]1[N:14]=[N:15][N:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20](Br)[CH:19]=2)[N:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[CH3:26][N:27](C=O)C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].[C-]#N.[Zn+2].[C-]#N.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].C([O-])(=O)C.[Zn+2].C([O-])(=O)C.[Zn]>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13]1[N:14]=[N:15][N:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:26]#[N:27])[CH:19]=2)[N:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 59212611HCID 59212611, compound

Product 1

HCID 59212606HCID 59212606, compoundYield 43%

Reagents, catalysts & solvents 5

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 11192Zinc AcetateCatalystHCID 23994ZincCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

The title compound of Example 13.1 (4.97 g, 12.61 mmol), dppf (0.042 g, 0.076 mmol), zinc cyanide (0.89, 7.57 mmol), Pd2(dba)3 (0.026 g, 0.025 mmol), zinc acetate (0.185 g, 1.01 mmol) and Zn dust (0.066 g, 1.01 mmol) were stirred in DMF (50 mL) and water (1.5 mL) for 12 h at 90° C. and a further 6 h at 120° C. The reaction mixture was partitioned between ethyl acetate and water. The organic extracts were dried over sodium sulphate, filtered and concentrated and purified by column chromatography to afford the title product (1.83 g, 43%).

Workup

  1. customa further 6 h
  2. customat 120° C
  3. customThe reaction mixture was partitioned between ethyl acetate and water
  4. dry with materialThe organic extracts were dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-ce2adbe8f870468d9c9ff225beb07535
Source dataset
uspto-grants-2010_03
Patent number
US07678796B2

Reaction notes

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