6-fluoro-1'-methyl-[3,4'-bipyridin]-2'(1'H)-one → (+/-)-4-(6-Fluoropyridin-3-yl)-1-methylpiperidin-2-one

HRID 595914Notes

Reaction equation

HRID 595914 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]([CH3:14])[C:10](=[O:15])[CH:9]=2)=[CH:4][CH:3]=1>CO.[Pd]>[F:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([CH3:14])[C:10](=[O:15])[CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 1180465486-fluoro-1'-methyl-[3,4'-bipyridin]-2'(1'H)-one

Product 1

HCID 118054587(+/-)-4-(6-Fluoropyridin-3-yl)-1-methylpiperidin-2-oneYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a steel bomb, a solution of 6-fluoro-1′-methyl-[3,4′-bipyridin]-2′(1′H)-one (340 mg, 1.665 mmol) in MeOH (remaining 60% head space) was added followed by addition of Pd—C (Degussa) (354 mg, 0.333 mmol). After degassing with nitrogen stream, the steel bomb was filled with hydrogen (250 psi). The reaction mixture was stirred overnight. The reaction mixture was filtered off through Celite (washed with EtOAc/MeOH). The volatile materials were concentrated in vacuo to give crude (+/−)-4-(6-fluoropyridin-3-yl)-1-methylpiperidin-2-one (341 mg, 1.638 mmol, 98% yield) which was used for the next step without further purification. LCMS (m/z): 209.1 (MH+), 0.47 min.

Workup

  1. customAfter degassing with nitrogen stream
  2. additionthe steel bomb was filled with hydrogen (250 psi)
  3. filtrationThe reaction mixture was filtered off through Celite (washed with EtOAc/MeOH)
  4. concentrationThe volatile materials were concentrated in vacuo

Sources & evidence

ORD record
ord-8c8d468d4e544a0998a64b52cfb0e9ab
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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