N-methyl-2-pyrrolidone → HCID 22632787, compound

HRID 2416619Notes

Reaction equation

HRID 2416619 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[O:8][CH2:9][C:10](=[O:20])[N:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2I)[N:12]=1.[CH3:21][N:22]1CCCC1=O>C(=O)(O)[O-].[Na+].[C-]#N.[Zn+2].[C-]#N.[Cu](I)I.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[O:8][CH2:9][C:10](=[O:20])[N:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:21]#[N:22])[N:12]=1

Participants

7

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 22632813HCID 22632813, compound

Product 1

HCID 22632787HCID 22632787, compoundYield 54%

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 83717Copper iodideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 516892Sodium BicarbonateSolvent

Procedure

2-(2-Pyridyl)-4-(2-iodophenyl)-4H-1,3,4-oxadiazine-5(6H)-one (100 mg) obtained in Example 105 was dissolved in N-methyl pyrrolidone (2 ml). Zinc cyanide (80 mg), copper iodide (5 mg) and tetrakis(triphenyl phosphine) palladium (10 mg) were added thereto, followed by stirring for 1 hour. The reaction solution was diluted with an aqueous saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the reaction solution was evaporated and purified by silica gel chromatography (hexane/ethyl acetate system), to give the title compound (40 mg, 54%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter the drying agent was filtered off
  5. customthe reaction solution was evaporated
  6. custompurified by silica gel chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-e58c2bce94f142e0ae925f3634c1ef4e
Source dataset
uspto-grants-2004_11
Patent number
US06825192B1

Reaction notes

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