Ammonia → HCID 19364861, compound

HRID 1531008Notes

Reaction equation

HRID 1531008 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:12]3=[C:13]([C:15](=[O:25])[C:16]([CH2:18][C:19]4[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=4)=[CH:17][N:11]3[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=3)[CH:14]=1.[NH3:26]>[Cu].[Cu](I)I>[NH2:26][C:2]1[CH:3]=[C:4]2[C:12]3=[C:13]([C:15](=[O:25])[C:16]([CH2:18][C:19]4[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=4)=[CH:17][N:11]3[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=3)[CH:14]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 21252812HCID 21252812, compound

Product 1

HCID 19364861HCID 19364861, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 83717Copper iodideCatalyst

Conditions

Temperature
185 °C

Procedure

2-bromo-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one (555 mg) produced in Example 178, copper (20 mg), and copper iodide (10 mg) were suspended in aqueous ammonia (28%, 30 ml) in a pressure-resistant microbomb, and the suspension was heated to 180 to 190° C. in an oil bath and stirred for 8 hours. The reaction mixture was then allowed to cool and brought back to normal pressure, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: ethyl acetate), and the crude purification product was recrystallized from ethanol to obtain the title compound (120 mg; 26%).

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel flash column chromatography (eluent: ethyl acetate)
  7. customthe crude purification product
  8. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-4bd32c93f3cc4b09b24767d6bfb29973
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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