HCID 69673612, compound → HCID 69673185, compound

HRID 2283255Notes

Reaction equation

HRID 2283255 reaction equation
[C:1]1([C:7]2[N:8]=[N:9][CH:10]=[C:11]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:12]=2[C:13]2[O:14][CH:15]=[C:16]([CH:18]=[CH2:19])[N:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.[Pd]>[C:1]1([C:7]2[N:8]=[N:9][CH:10]=[C:11]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:12]=2[C:13]2[O:14][CH:15]=[C:16]([CH2:18][CH3:19])[N:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 69673612HCID 69673612, compound

Product 1

HCID 69673185HCID 69673185, compoundYield 24.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(3,5-diphenylpyridazin-4-yl)-4-vinyloxazole (25 mg, 0.07 mmol) in methanol (4 mL), 10% Pd/C (20 mg, wt/wt) was added and the reaction mixture was stirred under hydrogen atmosphere for 2 h. The reaction mixture was filtered through a celite bed and washed with methanol. Solvent was evaporated under reduced pressure to obtain the crude product that was purified by column chromatography (100-200 mesh silica gel 25% EtOAc-Hexane) to furnish 2-(3,5-diphenylpyridazin-4-yl)-4-ethyloxazole (compound 22) (5.7 mg, 22%) as a pale yellow gummy liquid.

Workup

  1. filtrationThe reaction mixture was filtered through a celite bed
  2. washwashed with methanol
  3. customSolvent was evaporated under reduced pressure
  4. customto obtain the crude product that
  5. customwas purified by column chromatography (100-200 mesh silica gel 25% EtOAc-Hexane)

Sources & evidence

ORD record
ord-fc771c37a8614c15bfb1b7bc4b6cbbdc
Source dataset
uspto-grants-2015_09
Patent number
US09145372B2

Reaction notes

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