Dimethylformamide → HCID 66664935, compound

HRID 1773548Notes

Reaction equation

HRID 1773548 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([O:16][CH3:17])[C:8]([NH:12][C:13](=[O:15])[CH3:14])=[CH:9]2)=[CH:4][CH:3]=1.[CH3:18][N:19](C)C=O>[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].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].O>[C:18]([C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([O:16][CH3:17])[C:8]([NH:12][C:13](=[O:15])[CH3:14])=[CH:9]2)=[CH:4][CH:3]=1)#[N:19]

Participants

7

Reactant 2

HCID 6228DimethylformamideHCID 58056199HCID 58056199, compound

Product 1

HCID 66664935HCID 66664935, compound

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent2×

Conditions

Temperature
120 °C

Procedure

To a solution of N-(7-bromo-3-methoxy-naphthalen-2-yl)-acetamide (1.2 g, 4.0 mmol) in a previously degassed mixture of water and N,N-dimethylformamide (3/1, 40 mL) was added zinc cyanide (0.28 g, 2.4 mmol) followed by tris(dibenzylideneacetone)dipalladium(0) (0.18 g, 0.22 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (0.27 g, 0.48 mmol) and the resulting mixture was heated at 120° C. overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The organic extracts were washed 3 times with water, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (hexane/EtOAc) to afford 0.621 g of N-(7-cyano-3-methoxy-naphthalen-2-yl)-acetamide as a cream colored solid. MS=241 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts were washed 3 times with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude residue was purified by flash chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-40ce3ff12c934696bad64fd37b18991f
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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