HCID 118558022, compound → HCID 118557955, compound

HRID 2207200Notes

Reaction equation

HRID 2207200 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1/[CH:8]=[C:9]1/[C:10](=[O:19])[C:11]2[C:16]([CH2:17]/1)=[CH:15][C:14]([CH3:18])=[CH:13][CH:12]=2>CCO.[Pt]>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH3:18])[CH:15]=2)[C:10]1=[O:19]

Participants

4

Reactant 1

HCID 118558022HCID 118558022, compound

Product 1

HCID 118557955HCID 118557955, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

Pt/C (5 wt % loading, 125 mg) was added to a stirred solution of the compound 90 (1.24 g, 4 mmol) in EtOH (40 mL) at room temperature. The resulting suspension was stirred for 3 hours under H2 atmosphere (1 atm) then filtered over Celite, rinsed with dichloromethane and concentrated to dryness. The crude residue was purified by column chromatography on SiO2 (gradient of EtOAc in petroleum ether) to afford the title compound 105 as a white solid (Yield 0.75 g, 59%).

Workup

  1. filtrationthen filtered over Celite
  2. washrinsed with dichloromethane
  3. concentrationconcentrated to dryness
  4. customThe crude residue was purified by column chromatography on SiO2 (gradient of EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-280063025352499fae436468bb424585
Source dataset
uspto-grants-2016_06
Patent number
US09376387B2

Reaction notes

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