2-Bromopyridine → HCID 15123334, compound

HRID 650567Notes

Reaction equation

HRID 650567 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.CCCCCC.[CH2:19]([N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][C:27]1=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1C[O:36]CC1>>[CH2:19]([N:26]1[CH2:31][CH2:30][C:29]([OH:36])([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 5

HCID 79732-BromopyridineHCID 8028TetrahydrofuranHCID 8058HexaneHCID 51700761-Benzyl-2-piperidoneHCID 178418339Butyllithium

Product 1

HCID 15123334HCID 15123334, compoundYield 66.41%

Procedure

To a stirred solution of 2-bromopyridine (10 mmol) in THF (120 mL) at −78° C. under argon, 2.5 M n-butyl lithium solution in hexane (4.5 mL, 11.25 mmol) was injected over 5 min. After 25 min, 1-benzylpiperidone (10 mmol) was added neat. After 30 min, the mixture was quenched by addition of aqueous NH4Cl solution (50 mL). The mixture diluted with ethyl acetate (200 mL), washed with brine (150 mL), dried (Na2SO4). Solvent was evaporated and the residue was purified by column chromatography (silica gel, EtOAc/Hexane from 20% to 60%) to give the desired product(1.78 g, 66.41% ). 1H-NMR was consistent with the structure.

Workup

  1. waitAfter 30 min
  2. customthe mixture was quenched by addition of aqueous NH4Cl solution (50 mL)
  3. additionThe mixture diluted with ethyl acetate (200 mL)
  4. washwashed with brine (150 mL)
  5. dry with materialdried (Na2SO4)
  6. customSolvent was evaporated
  7. customthe residue was purified by column chromatography (silica gel, EtOAc/Hexane from 20% to 60%)

Sources & evidence

ORD record
ord-8103265a0eec4ba5bab5a87d85a4f59f
Source dataset
uspto-grants-2001_08
Patent number
US06274585B1

Reaction notes

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