HCID 86229373, compound → 1-((6-ethylpyridin-3-yl)methyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one

HRID 1948281Notes

Reaction equation

HRID 1948281 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][C:6]([CH2:9][N:10]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[CH:13]=[CH:12][C:11]2=[O:24])=[CH:5][CH:4]=1)#[CH:2]>CO.[Pd]>[CH2:1]([C:3]1[N:8]=[CH:7][C:6]([CH2:9][N:10]2[CH:15]=[C:14]([C:16]3[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)[CH:13]=[CH:12][C:11]2=[O:24])=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 86229373HCID 86229373, compound

Product 1

HCID 589669071-((6-ethylpyridin-3-yl)methyl)-5-(4-methoxyphenyl)pyridin-2(1H)-oneYield 62.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

According to Scheme 33 Step 3: To a suspension of Pd/C 10% (0.05 eq) in MeOH (10 mL) under N2 atmosphere, a solution of 1-((6-ethynylpyridin-3-yl)methyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one (0.15 mmol, 48 mg) was added at room temperature. The flask was evacuated and filled with hydrogen until the pressure reached 20 psi. The resulting suspension was shaken at room temperature for 1 hour. The catalyst was filtered off and the filtrate was evaporated under vacuum to give a residue. The residue was purified in a circular chromatography-TLC CH2Cl2/MeOH(NH3)sat. 2% yielding 1-((6-ethylpyridin-3-yl)methyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one (30 mg, 61%).

Workup

  1. customThe flask was evacuated
  2. additionfilled with hydrogen until the pressure
  3. filtrationThe catalyst was filtered off
  4. customthe filtrate was evaporated under vacuum
  5. customto give a residue
  6. customThe residue was purified in a circular chromatography-TLC CH2Cl2/MeOH(NH3)sat

Sources & evidence

ORD record
ord-9dc32c85029c47c7a30744927bdcf862
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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