Dimethylformamide → HCID 68455479, compound

HRID 2357648Notes

Reaction equation

HRID 2357648 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=3[CH3:22])[C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1.[CH3:23][N:24](C=O)C>C(OCC)(=O)C.[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.C(Cl)(Cl)Cl.[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]>[C:23]([C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=3[CH3:22])[C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1)#[N:24]

Participants

7

Reactant 2

HCID 6228DimethylformamideHCID 77230175Methyl 3-(1-chlorophthalazin-6-yl)-4-methylbenzoate

Product 1

HCID 68455479HCID 68455479, compound

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To methyl 3-(1-chlorophthalazin-6-yl)-4-methylbenzoate (2.49 g, 7.96 mmol) and zinc cyanide (1.87 g, 15.9 mmol) was added DMF (39.8 mL). The mixture was sparged with nitrogen for 15 min, and tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (0.330 g, 0.318 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (0.177 g, 0.318 mmol) were added. The reaction was heated to 100° C. for 30 min. The reaction mixture was diluted with 100 mL ethyl acetate, partitioned with sodium bicarbonate (saturated, aqueous), and the organics were washed 3×50 mL with sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, concentrated in vacuo, and purified by flash chromatography to give the title compound. MS (ES+): 304(M+H)+.

Workup

  1. customThe mixture was sparged with nitrogen for 15 min
  2. custompartitioned with sodium bicarbonate (saturated, aqueous)
  3. washthe organics were washed 3×50 mL with sodium bicarbonate (saturated, aqueous)
  4. customseparated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-0c140700ee914f95afbe6dbd4487d259
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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