Pyridine → HCID 58203507, compound

HRID 1289040Notes

Reaction equation

HRID 1289040 reaction equation
[CH2:1]([N:5]1[C:10]([O:11][C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[CH:13]=2)=[C:9]([CH:20]([CH3:22])[CH3:21])[C:8](=[O:23])[NH:7][C:6]1=[O:24])[C:2]#[C:3][CH3:4].N1C=CC=CC=1.N1C2C(=CC=CC=2)C=CC=1>CO.[Pd]>[CH2:1]([N:5]1[C:10]([O:11][C:12]2[CH:13]=[C:14]([CH3:19])[CH:15]=[C:16]([CH3:18])[CH:17]=2)=[C:9]([CH:20]([CH3:21])[CH3:22])[C:8](=[O:23])[NH:7][C:6]1=[O:24])/[CH:2]=[CH:3]\[CH3:4]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7047QuinolineHCID 18925251HCID 18925251, compound

Product 1

HCID 58203507HCID 58203507, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 33 mg (0.1 mmol) of the compound obtained from Example 11 in 1 ml of methanol were added 3 ml of pyridine, a drop of quinoline, and 4 mg of palladium on barium sulfate. The reaction mixture was then stirred for about 2 hours at room temperature under an atmosphere of hydrogen, filtered through Cellite pad, and evaporated under reduced pressure to give a light brown oil, which was purified by flash chromatography using a mixture of ethyl acetate and hexane (1:3) as an eluent to afford 25 mg (yield 76%) of the title compound as a white solid.

Workup

  1. filtrationfiltered through Cellite pad
  2. customevaporated under reduced pressure
  3. customto give a light brown oil, which
  4. customwas purified by flash chromatography
  5. additiona mixture of ethyl acetate and hexane (1:3) as an eluent

Sources & evidence

ORD record
ord-1b47d8f5ded446edb2a0a3abf74a3bc5
Source dataset
uspto-grants-1998_05
Patent number
US05747500

Reaction notes

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