HCID 118046042, compound → HCID 118045832, compound

HRID 595822Notes

Reaction equation

HRID 595822 reaction equation
[S:1]1[CH2:5][CH2:4][C:3]([C:6]2[CH:7]=[CH:8][C:9]([NH2:12])=[N:10][CH:11]=2)=[CH:2]1>C(O)C.[Pd]>[S:1]1[CH2:5][CH2:4][CH:3]([C:6]2[CH:7]=[CH:8][C:9]([NH2:12])=[N:10][CH:11]=2)[CH2:2]1

Participants

4

Reactant 1

HCID 118046042HCID 118046042, compound

Product 1

HCID 118045832HCID 118045832, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-(4,5-dihydrothiophen-3-yl)pyridin-2-amine(0.78 g, 4.38 mmol) was dissolved in ethanol(30 mL), to it was added Pd—C (Deggussa, 10%, 0.233 g) and the mixture was stirred under H2 balloon overnight. The reaction was not complete by LCMS. The Pd—C catalyst was removed by filtering through a Celite pad, and to the filtrate was added new Pd—C catalyst (0.24 g), and the mixture was stirred under H2 balloon under same condition for another 6 h. The reaction mixture was filtered off through Celite pad, and the filtrate was concentrated under reduced pressure yielding 5-(tetrahydrothiophen-3-yl)pyridin-2-amine (0.661 g, 84%) as colorless oil. LCMS (m/z): 181.2 (MH+), 0.39 min.

Workup

  1. customThe Pd—C catalyst was removed
  2. filtrationby filtering through a Celite pad
  3. additionto the filtrate was added new Pd—C catalyst (0.24 g)
  4. stirringthe mixture was stirred under H2 balloon under same condition for another 6 h
  5. filtrationThe reaction mixture was filtered off through Celite pad
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a35bde19c519411da22d1528212eb358
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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