6'-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-[3,3'-bipyridin]-6(1H)-one → 5-(6-Fluoropyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)piperidin-2-one

HRID 595909Notes

Reaction equation

HRID 595909 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11](=[O:14])[N:10]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:9]=2)=[CH:4][CH:3]=1>CO.[Pd]>[F:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:9][N:10]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:21])([CH3:20])[CH3:22])[C:11](=[O:14])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 1240240426'-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-[3,3'-bipyridin]-6(1H)-one

Product 1

HCID 1232474535-(6-Fluoropyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)piperidin-2-oneYield 92.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a steel bomb, a solution of 6′-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-[3,3′-bipyridin]-6(1H)-one (311 mg, 0.971 mmol) in MeOH (remaining 60% head space) was added followed by addition of Pd—C (207 mg, 0.194 mmol). After degassing with nitrogen stream, the steel bomb was pressurized with hydrogen gas up to 250 psi. The reaction was stirred at room temperature for 20 h. LCMS—0.9 min MH+325.1 (single major). The reaction mixture was filtered off through Celite (washed with EtOAc). The volatile materials were concentrated in vacuo to give crude 5-(6-fluoropyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)piperidin-2-one (290 mg, 0.894 mmol, 92%), which was used for the next step without further purification.

Workup

  1. customAfter degassing with nitrogen stream
  2. custom0.9 min MH
  3. filtrationThe reaction mixture was filtered off through Celite (washed with EtOAc)
  4. concentrationThe volatile materials were concentrated in vacuo

Sources & evidence

ORD record
ord-3edc5ace1b174de1a1650d2368d09d5c
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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