Water → HCID 54596679, compound

HRID 1747561Notes

Reaction equation

HRID 1747561 reaction equation
I[C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([O:19][CH:20]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[C:21]([F:24])([F:23])[F:22])[C:8]([NH:12][S:13]([CH2:16][CH2:17][CH3:18])(=[O:15])=[O:14])=[N:9]2)=[CH:4][CH:3]=1.O.C[C:33]([N:35](C)C)=O>[C-]#N.[Zn+2].[C-]#N.[Zn].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]>[C:33]([C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([O:19][CH:20]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[C:21]([F:24])([F:22])[F:23])[C:8]([NH:12][S:13]([CH2:16][CH2:17][CH3:18])(=[O:14])=[O:15])=[N:9]2)=[CH:4][CH:3]=1)#[N:35]

Participants

8

Reactant 3

HCID 962WaterHCID 31374DimethylacetamideHCID 71294052HCID 71294052, compound

Product 1

HCID 54596679HCID 54596679, compoundYield 42%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
120 °C

Procedure

Compound 77 (41.0 mg, 0.074 mmol) obtained in Example 74 was dissolved in DMA (1.60 mL). To the solution were added zinc cyanide (21.8 mg, 1.11 mmol), zinc (1.17 mg, 0.018 mmol), tris(dibenzylideneacetone)dipalladium (2.72 mg, 0.003 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (2.67 mg, 0.005 mmol), and the mixture was stirred at 120° C. for 1 hour. Water was added to the reaction mixture and the mixture was filtered through Celite. The filtrate was extracted with ethyl acetate. Washing with saturated brine and drying over anhydrous magnesium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 2/3) to give Compound 78 (14.0 mg, 42% yield).

Workup

  1. filtrationthe mixture was filtered through Celite
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washWashing with saturated brine
  4. dry with materialdrying over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent in the filtrate was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 2/3)

Sources & evidence

ORD record
ord-c0abb16aa0eb4e0391ab50a6e6306350
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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